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WO2018016742A1 - Novel heterocyclic compound and organic light-emitting device using same - Google Patents

Novel heterocyclic compound and organic light-emitting device using same Download PDF

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Publication number
WO2018016742A1
WO2018016742A1 PCT/KR2017/006274 KR2017006274W WO2018016742A1 WO 2018016742 A1 WO2018016742 A1 WO 2018016742A1 KR 2017006274 W KR2017006274 W KR 2017006274W WO 2018016742 A1 WO2018016742 A1 WO 2018016742A1
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compound
llozw
oav
8ΐοζ
substituted
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French (fr)
Korean (ko)
Inventor
정민우
이동훈
박태윤
조성미
문정욱
이정하
채미영
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LG Chem Ltd
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LG Chem Ltd
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Priority claimed from KR1020170075029A external-priority patent/KR101849747B1/en
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to CN201780004123.4A priority Critical patent/CN108368078B/en
Priority to US15/771,066 priority patent/US11903311B2/en
Priority to EP17831215.3A priority patent/EP3480194B1/en
Priority to JP2019502221A priority patent/JP7210856B2/en
Publication of WO2018016742A1 publication Critical patent/WO2018016742A1/en
Anticipated expiration legal-status Critical
Priority to US17/842,520 priority patent/US12167689B2/en
Ceased legal-status Critical Current

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    • 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
    • C07D405/02—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
    • C07D405/10—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 linked by a carbon chain containing aromatic rings
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
    • C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
    • 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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • 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
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene

Definitions

  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, many studies have been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode.
  • the organic layer is often formed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • Patent Document 0001 Korean Patent Publication No. 10-2000-0051826
  • the present invention relates to a novel heterocyclic compound compound and a light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula (1).
  • 3 ⁇ 4 is 0 or S
  • Li and L 2 are each independently a single bond; A substituted or unsubstituted C 6 - 60 arylene; Or substituted or unsubstituted 0, N, Si and S containing at least one hetero atom selected from the group consisting of ( 60 heteroarylene,
  • Yi to Y3 are each independently N or CR 3 , at least one of ⁇ to Y 3 is ⁇ ,
  • Ar 2 is substituted or unsubstituted C 6 -60 aryl
  • Ri to 3 ⁇ 4 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-60 alkyl; Substituted or unsubstituted d-60 Haloalkyl; Substituted or unsubstituted d- 60 alkoxy; Substituted or unsubstituted d-60 haloalkoxy; Substituted or unsubstituted C 3 -60 cycloalkyl; Substituted or unsubstituted
  • nl and n2 are each independently an integer of 0-3.
  • the present invention is a crab 1 electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1. to provide.
  • the compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode.
  • the compound represented by Chemical Formula 1 may be used as a host material of the light emitting layer.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is.
  • a bond connected to another substituent means a bond connected to another substituent, a single bond means a case where no separate atoms are present in the portion represented by and L 2 .
  • the ester group may be substituted with a linear, branched or cyclic alkyl group having 6 to 25 carbon atoms or 6 to aryl carbon atoms in the oxygen of the ester group.
  • the compound of the following structural formulae but is not limited thereto.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25.
  • it may be a compound having a structure as follows, but is not limited thereto.
  • the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the boron group is specifically trimethyl boron group, triethyl boron group, t-butyl dimethyl boron group, triphenyl boron group, phenyl boron group and the like, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1_ethyl-butyl, pentyl, n_ Pentyl, isopentyl, neopentyl, tert-pentyl, nuclear chamber, n-nuclear chamber, 1-methylpentyl, 2-methyltyl, 4-methyl-2-pentyl, 3, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylnucleus, cyclopentylmethyl, cyclonuxylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylnuclear, 2-propyl
  • the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2, 2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl— 1-yl, 2, 2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, and the like.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group.
  • the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryleneyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the fluorenyl group
  • the heterocyclic group is a heterocyclic group including one or more of 0, N, Si, and S as heterologous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heterocyclic group examples include thiophene group, furan group, pyr group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group and triazole group , Acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group , Quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, Benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, ,
  • the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above.
  • the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above.
  • the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group.
  • the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above.
  • the description of the aryl group described above may be applied.
  • the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description about the aryl group or cycloalkyl group described above may be applied except that two substituents are formed by bonding.
  • the heterocyclic ring is not monovalent, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding.
  • the present invention provides a compound represented by the formula (1). Specifically, the compound represented by Chemical Formula 1 is represented by the following Chemical Formulas 1-1 to 1-4:
  • Formulas 1-1 to 1-4 Yi to Y 3 , Ar la , Ar lb> Ar 2 , Ri, R 2 , nl and n2 are the same as defined in Formula 1 above.
  • L 2 are each independently, a single bond; Or a substituted or unsubstituted C 6 - 20 aryl may renil.
  • L 2 are each independently a single bond; Substituted or unsubstituted phenylene; Substituted or unsubstituted naphthylene; Or substituted or unsubstituted biphenylylene.
  • L 2 may be each independently, a single bond, or any one selected from the group consisting of:
  • ⁇ Is ⁇ , ⁇ 2 is CR 3 and Y 3 is CR 3 ;
  • ⁇ Is an ⁇ , ⁇ 2 is CH, ⁇ is 3 or ⁇ ;
  • ⁇ Is CH, ⁇ 2 is CH, and ⁇ 3 may be ⁇ .
  • X 2 is S, NZ 4 , or CZ 5 Z 6 ,
  • Zi to Z 6 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-20 alkyl; Substituted or unsubstituted d-20 haloalkyl; Substituted or unsubstituted C 6 - 20 aryl; Or heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, 0 and S,
  • cl is an integer of 0 to 5
  • c2 is an integer of 0 to 4,
  • c3 is an integer of 0-3. At this time, cl represents the number of ⁇ . When cl is 2 or more, two or more ⁇ may be the same or different from each other. Description of c2 and c3 can be understood with reference to the description of cl and the structure of the formula. Specifically, for example, Ar la and Ar lb may each independently be any one selected from the group consisting of:
  • Ar 2 is substituted or unsubstituted C 6 -60 aryl.
  • aryl does not include a non-aromatic condensed ring.
  • the substituted or unsubstituted fluorenyl group is excluded from Ar 2 of the present invention.
  • Ar 2 is unsubstituted or deuterium; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d- 60 alkyl; Substituted or unsubstituted d-60 haloalkyl; Si (3 ⁇ 4) (3 ⁇ 4) (3 ⁇ 4); 60 is an aryl, - C (Q 4) ( Q 5) (Q 6) and C 6 - C 6 substitution of from the group consisting of 60 to aryl substituents each independently selected
  • Qi to Q 6 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or ' unsubstituted d-20 alkyl; Or substitution It may be a 20-aryl-unsubstituted C 6.
  • Ar 2 can be any one selected from the group consisting of:
  • Zn to X 14 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-60 alkyl; Substituted or unsubstituted d-eo haloalkyl; Si (3 ⁇ 4) (3 ⁇ 4) (3 ⁇ 4); C (Q 4 ) (3 ⁇ 4) (3 ⁇ 4) and C 6 -60 aryl,
  • 3 ⁇ 4 to 3 ⁇ 4 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-20 alkyl; Or a substituted or unsubstituted C 6 ring - A 20 aryl,
  • cll is an integer from 0 to 5
  • cl2 is an integer of 0-7.
  • cl3 is an integer of 0 to 9
  • cl4 is an integer of 0 to 4
  • cl5 is an integer of 0 to 3
  • cl6 is an integer from 0 to 11
  • cl7 is an integer of 0 to 9
  • cl8 is an integer from 0 to 6
  • cl9 is an integer of 0-12. In this case, cll represents the number of Z u . When cll is 2 or more, two or more Z u may be the same or different from each other. Description of cl2 to cl9 can be understood with reference to the description of the cll and the structure of the formula.
  • 3 ⁇ 4 to Q 6 is hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; methyl; Or phenyl.
  • Ar 2 is any one selected from the group consisting of
  • Ri to 3 ⁇ 4 are each independently hydrogen; heavy hydrogen; Cyano; Or substituted or unsubstituted Cwo alkyl.
  • Ri and R 2 may each independently be hydrogen, deuterium, cyano, methyl, or methyl substituted with deuterium, and 3 ⁇ 4 may be hydrogen.
  • nl represents the number of. When nl is 2 or more, two or more 3 ⁇ 4 may be the same or different from each other. Description of n2 may be understood with reference to the description of nl and the structure of Formula 1.
  • the compound may be selected from the group consisting of the following compounds: oz
  • Compound represented by the formula (1) such as a pyridinyl group, a pyrimidinyl group, or a triazinyl group at a specific position of the dibenzofuran or dibenzothiophene core
  • the N atom-containing heteroaryl substituent group has a structure in which an aromatic aryl substituent is linked to a specific position of the dibenzofuran or dibenzothiophene core, whereby the organic light emitting device using the non-aromatic condensed cyclic group such as fluorenyl group is connected. Compared with the organic light emitting device using the compound, it can exhibit high efficiency, low driving voltage and long life.
  • the compound represented by the formula (1) can be prepared by a manufacturing method such as Banung Formula 1 as follows: In Reaction Formula 1, 1 2 , Yi to Y 3 , Aria, Ar lb and Ar 2 are the same as defined in Formula 1.
  • the compound represented by Formula 1 may be prepared by appropriately replacing the starting material in accordance with the structure of the compound to be prepared with reference to Banung Formula 1.
  • the present invention also provides an organic light emitting device including the compound represented by Chemical Formula 1.
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound represented by Chemical Formula 1. to provide.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1.
  • the compound represented by Chemical Formula 1 may be used as a host material in the emission layer.
  • the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 the structure of an organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
  • the compound represented by Formula 1 may be included in the light emitting layer.
  • 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is.
  • the compound represented by Chemical Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer.
  • the organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate by using a PVDC physical vapor deposition method such as sputtering or e-beam evaporat ion.
  • an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer and an electron transporting layer is formed thereon, by depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound represented by Chemical Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer anode material on a substrate from a cathode material (W0 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode.
  • As the anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material include metals such as vanadium, crumb, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide ( ⁇ ), indium zinc oxide (IZ0); ⁇ 0: ⁇ 1 or SN0 2 : A combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PED0T), polypyrrole and polyaniline, but are not limited to sons no. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from the electrode, the hole injection material has the ability to transport holes to have a hole injection effect at the anode, has an excellent hole injection effect to the light emitting layer or the light emitting material, The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • the highest occupied mol ecular orbital (HO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • the hole injection material include metal porphyr (in), oligothiophene, arylamine-based organics, nucleonitrile-nucleated azatriphenylene-based organics, quinacridone-based organics, and perylene ) Organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer receives holes from the hole injection layer
  • a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer as a hole transporting material is suitable.
  • Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • the light emitting insect may include a host material and a dopant material.
  • the host material may include a compound represented by Chemical Formula 1 described above. In addition, it may further include a condensed aromatic ring derivative or a hetero ring-containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives and ladder type furans.
  • Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes : fluoranthene compounds, metal complexes, and the like.
  • the aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene and periplanthene having an arylamino group, and the styrylamine compound may be substituted or unsubstituted.
  • arylamine As a compound in which at least one arylvinyl group is substituted, a substituent selected from one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • an electron transport material a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Do.
  • the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, etherboom and samarium, each followed by an aluminum or silver layer.
  • the electron injection layer is a layer for injecting electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from the cathode, has an excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds and nitrogen-containing five-membered ring derivatives; and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Manganese, tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis ( 10—hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl -8-quinolinato) (0-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphlato) aluminum, bis (2-methyl-8-quinolinato) (2 -Naphlato) gallium, etc., but is not limited thereto.
  • the organic light emitting device may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device. Preparation of the compound represented by Chemical Formula 1 and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
  • Phenylnaphthalene (l-brotno-4-phenylnaphthalene) (10.8 g, 38
  • Example 1 Synthesis Example 1 except that 4-chloro_2,6-diphenylpyrimidine (10.2 g, 38.1 mmol) was used instead of compound Q-36 19.9 g, 38.1 ⁇ ol) and 2-bromophenanthrene.
  • a glass substrate coated with a thin film having an indium tin oxide (IT0) of 1,300 A was placed in distilled water in which a detergent was dissolved and ultrasonically cleaned.
  • a detergent was used as the detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as the distilled water.
  • the ultrasonic cleaning was performed twice with distilled water for 10 minutes.
  • ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the HI-1 compound as described above was thermally vacuum deposited to a thickness of 50 A on the ⁇ transparent electrode prepared as above to form a hole injection layer.
  • a hole transport layer was formed by thermal vacuum deposition of the HT-1 compound at a thickness of 250 A on the hole injection layer, and an electron blocking layer was formed by vacuum deposition of the HT-2 compound at a thickness of 50 A on the HT-1 deposition film.
  • Phosphorescent dopant YGD-1 was co-deposited at a weight ratio of 1 and 13 ⁇ 4 to form a light emitting layer having a thickness of 400 A.
  • ET-1 material was vacuum deposited to a thickness of 250 A on the light emitting layer, and the ET-2 material was co-deposited with Li in a 2% weight ratio to a thickness of 100 A to form an electron transport layer and an electron injection layer.
  • Aluminum was deposited to a thickness of 1000 A on the electron injection layer to form a cathode.
  • the organic light emitting diodes of Examples 2 to 49 were manufactured by the same method as Example 1, except that phosphorescent host materials and dopant contents were changed as shown in Tables 1 to 3 below to form the emission layer. . Comparative Example 1 to Comparative Example 10
  • the organic light emitting diodes of Comparative Examples 1 to 10 were manufactured using the same method as in Example 1, respectively.
  • the host materials A to I used in the comparative examples are as follows.
  • T95 means the time required to reduce the luminance to 953 ⁇ 4 when the initial luminance at the light density of 50 mA / cm 2 is 100%.
  • a HI-1 compound as described below was thermally vacuum deposited to a thickness of 150 A to form a hole injection layer.
  • phosphorescent dopant GD-1 was co-deposited on the hole transport layer at a weight ratio of Compound 47 and 5% prepared in Synthesis Example 15-3 to form a light emitting layer having a thickness of 400 A.
  • a hole blocking layer was formed by vacuum depositing an ET-3 material to a thickness of 50 A on the light emitting layer, and a 250 A electron transport layer was formed by vacuum depositing an ET-4 material and LiQ in a weight ratio of 1: 1 on the hole blocking layer.
  • Lithium fluoride (UF) having a thickness of 10 A was sequentially deposited on the electron transport layer, and Mg was deposited with Ag at a weight ratio of 10> to form an electron injection layer having a thickness of 200 A.
  • Aluminum was deposited to a thickness of 1000A on the cathode to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.7 A / sec
  • the lithium fluoride of the cathode was maintained at 0.3 A / sec
  • the aluminum was maintained at the deposition rate of 2 A / sec. — 7 to 5 x 10 "8 torr
  • Example 50 Except for changing the phosphorescent host material and dopant content in forming the light emitting layer with Tables 4 and 5, the same method as in Example 50 was performed. Using each of the organic light emitting diodes of Examples 51 to 90, respectively. Comparative Examples 11 to 19
  • the organic light emitting diodes of Comparative Examples 11 to 19 were manufactured by the same method as Example 50, except that the phosphorescent host material and the dopant content were changed as shown in Table 6 when forming the emission layer.
  • the host materials A to I used in the comparative examples are as described above.
  • T95 means the time required for the luminance to decrease to 95% when the initial luminance at the light density of 20 mA / cm 2 is 100%.
  • the organic light emitting device manufactured by using the compound according to the present invention as a phosphorescent host material exhibits superior performance in terms of driving voltage, current efficiency, and lifetime compared to the organic light emitting device of the Comparative Example. can confirm.
  • the organic light emitting device according to the embodiment is a phosphorescence that is commonly used The lifespan was increased by at least 150% compared to the organic light emitting diodes according to Comparative Examples 9 and 19 using the compound I as a host material.
  • the organic light emitting device according to Examples 4, 8, and 50 is the organic light emitting device according to Comparative Examples 1, 6, 11, and 16 using compounds A and F having different substitution positions of the compound and triazinyl group according to the present invention, respectively.
  • the organic light emitting diode according to Example 28 also exhibited an increase in lifespan of about 370% or more compared to the organic light emitting diode according to Comparative Example 3 using the compound C.
  • the organic light emitting diode according to Examples 30 and 31 also includes Compound G. Compared to the organic light emitting device according to Comparative Example 7, using the above, the lifespan was increased by about 250% or more. In addition, it was found that the driving voltage, current efficiency, and lifespan of the organic light emitting diode according to Comparative Example 5 using the compound E containing no triazinyl group were significantly lower than those of the organic light emitting diode according to the embodiment.
  • the organic light emitting device according to Comparative Examples 8 and 18 using the compound H substituted with the dimethyl fluorenyl group also shows a significantly lower lifespan than the organic light emitting device according to the embodiment, which is used when manufacturing or driving the device. It is believed that this is due to the generation of impurities generated as radicals formed by dimethylfluorenyl in the air.

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Abstract

The present invention provides a novel heterocyclic compound and an organic light-emitting device using same.

Description

【명세서】  【Specification】

【발명의 명칭】  [Name of invention]

신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자  Novel heterocyclic compound and organic light emitting device using the same

【기술분야】  Technical Field

관련 출원 (들)과의 상호 인용  Cross Citation with Related Application (s)

본 출원은 2016년 7월 20일자 한국 특허 출원 제 10-2016-0092202호， 및 2017년 6월 14일자 한국 특허 출원 제 10-2017-0075029호에 기초한 우선권의 이익을 주장하며， 해당 한국 특허 출원들의 문헌에 개시된 모든 내용은 본 명세서의 일부로서 포함된다. 본 발명은 신규한 헤테로 고리 화합물 및 이를 포함하는 유기 발광 소자에 관한 것이다.  This application claims the benefit of priority based on Korean Patent Application No. 10-2016-0092202 dated July 20, 2016 and Korean Patent Application No. 10-2017-0075029 dated June 14, 2017, and the Korean patent application All content disclosed in these references is included as part of this specification. The present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.

【발명의 배경이 되는 기술】  [Technique to become background of invention]

일반적으로 유기 발광 현상이란 유기 물질을 이용하여 전기에너지를 빛에너지로 전환시켜주는 현상을 말한다. 유기 발광 현상을 이용하는 유기 발광 소자는 넓은 시야각， 우수한 콘트라스트， 빠른 응답 시간을 가지며， 휘도， 구동 전압 및 웅답 속도 특성이 우수하여 많은 연구가 진행되고 있다. 유기 발광 소자는 일반적으로 양극과 음극 및 상기 양극과 음극 사이에 유기물 층을 포함하는 구조를 가진다. 상기 유기물 층은 유기 발광 소자의 효율과 안정성을 높이기 위하여 각기 다른 물질로 구성된 다층의 구조로 이루어진 경우가 많으며， 예컨대 정공 주입층， 정공 수송층, 발광층， 전자수송층， 전자 주입층 등으로 이루어질 수 있다. 이러한 유기 발광 소자의 구조에서 두 전극 사이에 전압을 걸어주게 되면 양극에서는 정공이， 음극에서는 전자가 유기물 층에 주입되게 되고， 주입된 정공과 전자가 만났을 때 액시톤 (exci ton)이 형성되며， 이 엑시톤이 다시 바닥상태로 떨어질 때 빛이 나게 된다. 상기와 같은 유기 발광 소자에 사용되는 유기물에 대하여 새로운 재료의 개발이 지속적으로 요구되고 있다. 【선행기술문헌】 In general, organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material. The organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent luminance, driving voltage and response speed characteristics, many studies have been conducted. The organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode. The organic layer is often formed of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer. When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic layer, and excitons are formed when the injected holes and the electrons meet each other. When this exciton falls back to the ground, it glows. There is a continuous demand for the development of new materials for organic materials used in such organic light emitting devices. Prior Art Documents

【특허문헌】  [Patent literature]

(특허문헌 0001) 한국특허 공개번호 게 10-2000-0051826호  (Patent Document 0001) Korean Patent Publication No. 10-2000-0051826

【발명의 내용】  [Content of invention]

【해결하고자 하는 과제】  Problem to be solved

본 발명은 신규한 헤테로고리 화합물 화합물 및 이를 포함하 발광 소자에 관한 것이다.  The present invention relates to a novel heterocyclic compound compound and a light emitting device comprising the same.

【과제의 해결 수단】  [Measures of problem]

본 발명은 하기 화학식 1로 표시되는 화합물을 제공한다.  The present invention provides a compound represented by the following formula (1).

Figure imgf000003_0001
Figure imgf000003_0001

상기 화학식 1에서，  In Chemical Formula 1,

¾은 0또는 S이고,  ¾ is 0 or S,

Li 및 L2는 각각 독립적으로， 단일 결합; 치환 또는 비치환된 C6-60 아릴렌; 또는 치환 또는 비치환된 0， N , Si 및 S로 구성되는 군으로부터 선택되는 헤테로원자를 1개 이상 포함하는 ( 60 헤테로아릴렌이고， Li and L 2 are each independently a single bond; A substituted or unsubstituted C 6 - 60 arylene; Or substituted or unsubstituted 0, N, Si and S containing at least one hetero atom selected from the group consisting of ( 60 heteroarylene,

Yi 내지 Y3는 각각 독립적으로， N 또는 CR3이되， ^ 내지 Y3 중 적어도 하나는 Ν이고， Yi to Y3 are each independently N or CR 3 , at least one of ^ to Y 3 is Ν,

Arla및 는 각각 독립적으로， 치환 또는 비치환된 C6— 60 아릴; 또는 치환 또는 비치환된 N , 0 및 ' S로 구성되는 군으로부터 선택되는 헤테로원자를 1개 내지 3개 포함하는 d-so 헤테로아릴이고， Ar la and each independently represent a substituted or unsubstituted C 6 — 60 aryl; Or d-so heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of substituted or unsubstituted N, 0 and ' S,

Ar2는 치환 또는 비치환된 C6-60 아릴이고， Ar 2 is substituted or unsubstituted C 6 -60 aryl,

Ri 내지 ¾는 각각 독립적으로， 수소; 중수소; 할로겐; 시아노; 니트로 ; 아미노; 치환 또는 비치환된 d-60 알킬 ; 치환 또는 비치환된 d-60 할로알킬 ; 치환 또는 비치환된 d-60 알콕시 ; 치환 또는 비치환된 d-60 할로알콕시; 치환 또는 비치환된 C3-60 사이클로알킬; 치환 또는 비치환된Ri to ¾ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-60 alkyl; Substituted or unsubstituted d-60 Haloalkyl; Substituted or unsubstituted d- 60 alkoxy; Substituted or unsubstituted d-60 haloalkoxy; Substituted or unsubstituted C 3 -60 cycloalkyl; Substituted or unsubstituted

C2-6o 알케닐; 치환 또는 비치환된 C6-60 아릴; 치환 또는 비치환된 C6-60 아릴옥시; 또는 치환 또는 비치환된 N, 0 및 S로 구성되는 군으로부터 선택되는 헤테로원자를 1개 이상 포함하는 ( 60 헤테로아릴이고， C 2 -6o alkenyl; Substituted or unsubstituted C 6 -60 aryl; Substituted or unsubstituted C 6 -60 aryloxy; Or ( 60 heteroaryl) containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, 0 and S,

nl 및 n2는 각각 독립적으로， 0 내지 3의 정수이다. 또한, 본 발명은 게 1 전극; 상기 게 1 전극과 대향하여 구비된 제 2 전극; 및 상기 제 1 전극과 상기 제 2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서， 상기 유기물 층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는, 유기 발광 소자를 제공한다.  nl and n2 are each independently an integer of 0-3. In addition, the present invention is a crab 1 electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers comprises a compound represented by Chemical Formula 1. to provide.

【발명의 효과】  【Effects of the Invention】

상술한 화학식 1로 표시되는 화합물은 유기 발광 소자의 유기물 층의 재료로서 사용될 수 있으며， 유기 발광 소자에서 효율의 향상， 낮은 구동전압 및 /또는 수명 특성을 향상시킬 수 있다. 특히， 상술한 화학식 1로 표시되는 화합물은 발광층의 호스트 재료로 사용될 수 있다.  The compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting diode, and may improve efficiency, low driving voltage, and / or lifetime characteristics in the organic light emitting diode. In particular, the compound represented by Chemical Formula 1 may be used as a host material of the light emitting layer.

【도면의 간단한 설명】  [Brief Description of Drawings]

도 1은 기판 (1)， 양극 (2) , 발광층 (3)， 음극 (4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다.  FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.

도 2는 기판 (1)， 양극 (2)， 정공 주입층 (5)， 정공 수송층 (6)， 발광층 (7)， 전자수송층 (8) 및 음극 (4)로 이루어진 유기 발광 소자의 예를 도시한 것이다.  2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is.

【발명을 실시하기 위한 구체적인 내용】  [Specific contents to carry out invention]

이하， 본 발명의 이해를 돕기 위하여 보다 상세히 설명한다.  Hereinafter, in order to help the understanding of the present invention will be described in more detail.

본 명세서에서， 는 다른 치환기에 연결되는 결합을 의미하고， 단일 결합은 및 L2로 표시되는 부분에 별도의 원자가 존재하지 않은 경우를 의미한다 . 본 명세서에서 "치환 또는 비치환된1' 이라는 용어는 중수소; 할로겐기; 시아노기; 니트릴기; 니트로기; 히드록시기; 카보닐기; 에스테르기; 이미드기; 아미노기; 포스핀옥사이드기; 알콕시기; 아릴옥시기; 알킬티옥시기; 아릴티옥시기; 알킬술폭시기; 아릴술폭시기; 실릴기; 붕소기; 알킬기; 사이클로알킬기; 알케닐기; 아릴기; 아르알킬기; 아르알케닐기; 알킬아릴기; 알킬아민기; 아랄킬아민기; 헤테로아릴아민기; 아릴아민기; 아릴포스핀기; 또는 N, 0 및 S 원자 중 1개 이상을 포함하는 헤테로아릴로 이루어진 군에서 선택된 1개 이상의 치환기로 치환 또는 비치환되거나， 상기 예시된 치환기 중 2 아상의 치환기가 연결된 치환 또는 비치환된 것을 의미한다. 예컨대， "2 이상의 치환기가 연결된 치환기 "는 바이페닐기일 수 있다. 즉, 바이페닐기는 아릴기일 수도 있고， 2개의 페닐기가 연결된 치환기로 해석될 수도 있다. 본 명세서에서 카보닐기의 탄소수는 특별히 한정되지 않으나, 탄소수 1 내지 40인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나， 이에 한정되는 것은 아니다. In the present specification, means a bond connected to another substituent, a single bond means a case where no separate atoms are present in the portion represented by and L 2 . As used herein, the term "substituted or unsubstituted 1 'is deuterium; halogen group; cyano group; nitrile group; nitro group; hydroxy group; carbonyl group; ester group; imide group; amino group; phosphine oxide group; alkoxy group; aryl Oxy group; alkyl thioxy group; aryl thioxy group; alkyl sulfoxy group; aryl sulfoxy group; silyl group; boron group; alkyl group; cycloalkyl group; alkenyl group; aryl group; aralkyl group; aralkenyl group; alkylaryl group; alkylamine group Or an aralkylamine group; a heteroarylamine group; an arylamine group; an arylphosphine group; or an unsubstituted or substituted with one or more substituents selected from the group consisting of heteroaryl containing one or more of N, 0 and S atoms; It means that the substituent is substituted or unsubstituted in the two substituents of the above-described substituents, for example, "substituents in which two or more substituents are linked" may be a biphenyl group. The carbonyl group of the carbonyl group is not particularly limited, but is preferably 1 to 40. Specifically, the compound may be a compound having the following structure: Or not limited thereto.

Figure imgf000005_0001
본 명세서에 있어서， 에스테르기는 에스테르기의 산소가 탄소수 내지 25의 직쇄, 분지쇄 또는 고리쇄 알킬기 또는 탄소수 6 내지 아릴기로 치환될 수 있다. 구체적으로， 하기 구조식의 화합물이 될 있으나， 이에 한정되는 것은 아니다.
Figure imgf000006_0001
본 명세서에 있어서, 이미드기의 탄소수는 특별히 한정되지 않으나， 탄소수 1 내지 25인 것이 바람직하다. 구체적으로 하기와 같은 구조의 화합물이 될 수 있으나， 이에 한정되는 것은 아니다.
Figure imgf000005_0001
In the present specification, the ester group may be substituted with a linear, branched or cyclic alkyl group having 6 to 25 carbon atoms or 6 to aryl carbon atoms in the oxygen of the ester group. Specifically, the compound of the following structural formulae, but is not limited thereto.
Figure imgf000006_0001
In this specification, although carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.

Figure imgf000006_0002
본 명세서에 있어서， 실릴기는 구체적으로 트리메틸실릴기, 트리에틸실릴기， t-부틸디메틸실릴기， 비닐디메틸실릴기， 프로필디메틸실릴기, 트리페닐실릴기， 디페닐실릴기， 페닐실릴기 등이 있으나 이에 한정되지 않는다. 본 명세서에 있어서， 붕소기는 구체적으로 트리메틸붕소기， 트리에틸붕소기， t-부틸디메틸붕소기, 트리페닐붕소기， 페닐붕소기 등이 있으나 이에 한정되지 않는다. 본 명세서에 있어서， 할로겐기의 예로는 불소， 염소， 브롬 또는 요오드가 있다. 본 명세서에 있어서， 상기 알킬기는 직쇄 또는 분지쇄일 수 있고， 탄소수는 특별히 한정되지 않으나 1 내지 40인 것이 바람직하다, 일 실시상태에 따르면， 상기 알킬기의 탄소수는 1 내지 20이다. 또 하나의 실시상태에 따르면， 상기 알킬기의 탄소수는 1 내지 10이다. 또 하나의 실시상태에 따르면， 상기 알킬기의 탄소수는 1 내지 6이다. 알킬기의 구체적인 예로는 메틸, 에틸， 프로필， n-프로필， 이소프로필， 부틸, n-부틸 이소부틸， tert-부틸， sec-부틸， 1-메틸-부틸， 1_에틸-부틸， 펜틸， n_펜틸， 이소펜틸， 네오펜틸， tert-펜틸, 핵실， n-핵실, 1-메틸펜틸， 2-메틸 틸， 4-메틸 -2-펜틸， 3 , 3-디메틸부틸， 2-에틸부틸， 헵틸， n-헵틸， 1-메틸핵실， 사이클로펜틸메틸， 사이클로핵틸메틸， 옥틸， n-옥틸， tert-옥틸， 1- 메틸헵틸， 2-에틸핵실， 2-프로필펜틸， n-노닐， 2 , 2-디메틸헵틸， 1-에틸- 프로필， 1 , 1-디메틸-프로필， 이소핵실, 2-메틸펜틸, 4-메틸헥실， 5- 메틸핵실 등이 있으나， 이들에 한정되지 않는다. 본 명세서에 있어서, 상기 알케닐기는 직쇄 또는 분지쇄일 수 있고， 탄소수는 특별히 한정되지 않으나， 2 내지 40인 것이 바람직하다. 일 실시상태에 따르면， 상기 알케닐기의 탄소수는 2 내지 20이다. 또 하나의 실시상태에 따르면, 상기 알케닐기의 탄소수는 2 내지 10이다. 또 하나의 실시상태에 따르면， 상기 알케닐기의 탄소수는 2 내지 6이다. 구체적인 예로는 비닐， 1-프로페닐， 이소프로페닐， 1-부테닐， 2-부테닐, 3-부테닐， 1-펜테닐， 2-펜테닐， 3-펜테닐， 3-메틸 -1-부테닐， 1，3-부타디에닐， 알릴， 1-페닐비닐 -1-일, 2-페닐비닐 -1-일， 2 , 2-디페닐비닐 -1-일, 2-페닐 -2- (나프틸 -1-일)비닐— 1-일， 2 , 2-비스 (디페닐 -1-일)비닐 -1-일, 스틸베닐기, 스티레닐기 등이 있으나 이들에 한정되지 않는다. 본 명세서에 있어서， 사이클로알킬기는 특별히 한정되지 않으나， 탄소수 3 내지 60인 것이 바람직하며， 일 실시상태에 따르면， 상기 사이클로알킬기의 탄소수는 3 내지 30이다. 또 하나의 실시상태에 따르면， 상기 사이클로알킬기의 탄소수는 3 내지 20이다. 또 하나의 실시상태에 따르면， 상기 사이클로알킬기의 탄소수는 3 내지 6이다. 구체적으로 사이클로프로필， 사이클로부틸， 사이클로펜틸， 3-메틸사이클로펜틸， 2，3- 디메틸사이클로펜틸， 사이클로핵실， 3-메틸사이클로핵실, 4- 메틸사이클로핵실， 2 , 3-디메틸사이클로핵실， 3，4，5-트리메틸사이클로핵실， 4-tert-부틸사이클로핵실， 사이클로헵틸, 사이클로옥틸 등이 있으나, 이에 한정되지 않는다. 본 명세서에 었어서， 아릴기는 특별히 한정되지 않으나 탄소수 6 내지 60인 것이 바람직하며， 단환식 아릴기 또는 다환식 아릴기일 수 있다. 일 실시상태에 따르면， 상기 아릴기의 탄소수는 6 내지 30이다. 일 실시상태에 따르면， 상기 아릴기의 탄소수는 6 내지 20이다. 상기 아릴기가 단환식 아릴기로는 페닐기， 바이페닐기, 터페닐기 등이 될 수 있으나， 이에 한정되는 것은 아니다. 상기 다환식 아릴기로는 나프틸기， 안트라세닐기， 페난트릴기, 파이레닐기， 페릴레닐기， 크라이세닐기， 플루오레닐기 등이 될 수 있으나， 이에 한정되는 것은 아니다. 본 명세서에 있어서, 플루오레닐기는 치환될 수 있고， 치환기 2개가 서로 결합하여 스피로 구조를 형성할 수 있다. 상기 플루오레닐기가 ，
Figure imgf000006_0002
In the present specification, specifically, the silyl group includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. However, the present invention is not limited thereto. In the present specification, the boron group is specifically trimethyl boron group, triethyl boron group, t-butyl dimethyl boron group, triphenyl boron group, phenyl boron group and the like, but is not limited thereto. In the present specification, examples of the halogen group include fluorine, chlorine, bromine or iodine. In the present specification, the alkyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 1 to 40. According to one embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1_ethyl-butyl, pentyl, n_ Pentyl, isopentyl, neopentyl, tert-pentyl, nuclear chamber, n-nuclear chamber, 1-methylpentyl, 2-methyltyl, 4-methyl-2-pentyl, 3, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-heptyl, 1-methylnucleus, cyclopentylmethyl, cyclonuxylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylnuclear, 2-propylpentyl, n-nonyl, 2, 2- Dimethylheptyl, 1-ethyl-propyl, 1, 1-dimethyl-propyl, isonuclear chamber, 2-methylpentyl, 4-methylhexyl, 5-methylnuclear chamber, and the like, but is not limited thereto. In the present specification, the alkenyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms. Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2, 2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl— 1-yl, 2, 2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group, and the like. In the present specification, the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically Cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclonuclear chamber, 3-methylcyclonuclear chamber, 4-methylcyclonuclear chamber, 2, 3-dimethylcyclonuclear chamber, 3, 4, 5-trimethylcyclonuclear chamber, 4-tert-butylcyclonuclear chamber, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. As used herein, the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms. The aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto. The polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryleneyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto. In the present specification, the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure. The fluorenyl group,

Figure imgf000008_0001
Figure imgf000008_0001

등이 될 수 있다. 다만， 이에 한정되는 것은 아니다. 본 명세서에 있어서， 헤테로고리기는 이종 원소로 0， N , Si 및 S 중 1개 이상을 포함하는 헤테로고리기로서， 탄소수는 특별히 한정되지 않으나, 탄소수 2 내지 60인 것이 바람직하다. 헤테로고리기의 예로는 티오펜기， 퓨란기， 피를기， 이미다졸기， 티아졸기， 옥사졸기， 옥사디아졸기， 트리아졸기， 피리딜기， 비피리딜기， 피리미딜기， 트리아진기， 트리아졸기， 아크리딜기， 피리다진기， 피라지닐기, 퀴놀리닐기， 퀴나졸린기， 퀴녹살리닐기， 프탈라지닐기， 피리도 피리미디닐기， 피리도 피라지닐기， 피라지노 피라지닐기， 이소퀴놀린기， 인돌기， 카바졸기， 벤조옥사졸기， 벤조이미다졸기， 벤조티아졸기， 벤조카바졸기， 벤조티오펜기, 디벤조티오펜기, 벤조퓨라닐기， 페난쓰를린기 (phenanthrol ine) , 티아졸릴기， 이소옥사졸릴기, 옥사디아졸릴기， 티아디아졸릴기， 벤조티아졸릴기， 페노티아지닐기 및 디벤조퓨라닐기 등이 있으나， 이들에만 한정되는 것은 아니다. 본 명세서에 있어서， 아르알킬기， 아르알케닐기， 알킬아릴기， 아릴아민기 중의 아릴기는 전술한 아릴기의 예시와 같다. 본 명세서에 있어서， 아르알킬기, 알킬아릴기， 알킬아민기 중 알킬기는 전술한 알킬기의 예시와 같다. 본 명세서에 있어서, 헤테로아릴아민 중 헤테로아릴은 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 아르알케닐기 중 알케닐기는 전술한 알케닐기의 예시와 같다. 본 명세서에 있어서， 아릴렌은 2가기인 것을 제외하고는 전술한 아릴기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서, 헤테로아릴렌은 2가기인 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서， 탄화수소 고리는 1가기가 아니고， 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 아릴기 또는 사이클로알킬기에 관한 설명이 적용될 수 있다. 본 명세서에 있어서， 헤테로고리는 1가가가 아니고， 2개의 치환기가 결합하여 형성한 것을 제외하고는 전술한 헤테로고리기에 관한 설명이 적용될 수 있다. 한편 , 본 발명은 상기 화학식 1로 표시되는 화합물을 제공한다. 구체적으로， 상기 화학식 1로 표시되는 화합물은 하기 화학식 1-1 내지 1-4로 표시된다: And so on. However, the present invention is not limited thereto. In the present specification, the heterocyclic group is a heterocyclic group including one or more of 0, N, Si, and S as heterologous elements, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. Examples of the heterocyclic group include thiophene group, furan group, pyr group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group and triazole group , Acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group ， Quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group, indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, Benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthrol ine, thiazolyl group, isoxoxazolyl group, oxadiazolyl group, thiadiazolyl group, benzothiazolyl Groups, phenothiazinyl groups, dibenzofuranyl groups and the like, but are not limited thereto. In the present specification, the aryl group in the aralkyl group, aralkenyl group, alkylaryl group, and arylamine group is the same as the example of the aryl group described above. In the present specification, the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group is the same as the example of the alkyl group described above. In the present specification, the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group. In the present specification, the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above. In the present specification, except that the arylene is a divalent group, the description of the aryl group described above may be applied. In the present specification, the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group. In the present specification, the hydrocarbon ring is not a monovalent group, and the description about the aryl group or cycloalkyl group described above may be applied except that two substituents are formed by bonding. In the present specification, the heterocyclic ring is not monovalent, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding. On the other hand, the present invention provides a compound represented by the formula (1). Specifically, the compound represented by Chemical Formula 1 is represented by the following Chemical Formulas 1-1 to 1-4:

[화학식 1-1] [Formula 1-1]

Figure imgf000010_0001
Figure imgf000010_0001

[화학식 1-4]

Figure imgf000011_0001
상기 화학식 1-1 내지 1-4에서 , ， , Yi 내지 Y3, Arla, Arlb> Ar2, Ri, R2, nl 및 n2에 대한 설명은 상기 화학식 1에서 정의한 바와 같다. 바람직하게는， 상기 화학식 1에서， 및 L2는 각각 독립적으로， 단일 결합; 또는 치환 또는 비치환된 C6-20 아릴렌일 수 있다. 예를 들어， 및 L2는 각각 독립적으로， 단일 결합; 치환 또는 비치환된 페닐렌; 치환 또는 비치환된 나프틸렌; 또는 치환 또는 비치환된 바이페닐릴렌일 수 있다. 구체적으로 예를 들어， 및 L2는 각각 독립적으로， 단일 결합， 또는 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다: [Formula 1-4]
Figure imgf000011_0001
In Formulas 1-1 to 1-4,,, Yi to Y 3 , Ar la , Ar lb> Ar 2 , Ri, R 2 , nl and n2 are the same as defined in Formula 1 above. Preferably, in Formula 1, and L 2 are each independently, a single bond; Or a substituted or unsubstituted C 6 - 20 aryl may renil. For example, and L 2 are each independently a single bond; Substituted or unsubstituted phenylene; Substituted or unsubstituted naphthylene; Or substituted or unsubstituted biphenylylene. Specifically, for example, and L 2 may be each independently, a single bond, or any one selected from the group consisting of:

Figure imgf000012_0001
바람직하게는， 상기 화학식 1에서,
Figure imgf000012_0001
Preferably, in Formula 1,

^은 N이고， Y2는 Ν이고, Υ3는 Ν이거나; ^ Is N, Y 2 is Ν, Υ 3 is Ν;

^은 Ν이고， Υ2는 Ν이고， Υ3는 CR3아거나; ^ Is Ν, Υ 2 is Ν, Υ 3 is not CR 3 ;

^은 N이고， Y2는 CR3이고， Y3는 Ν이거나; ^ Is N, Y 2 is CR 3 and Y 3 is Ν;

^은 Ν이고， Υ2는 CR3이고， Y3는 CR3이거나; 또는 ^ Is Ν, Υ 2 is CR 3 and Y 3 is CR 3 ; or

^은 CR3이고, Y2는 CR3이고， Y3는 Ν일 수 있다. 바람직하게는， 상기 화학식 1에서， ^ Is CR 3 , Y 2 is CR 3 , and Y 3 may be Ν. Preferably, in Formula 1,

^은 Ν이고, Υ2는 Ν이고， Υ3는 Ν이거나; ^ Is Ν, Υ 2 is Ν, Υ 3 is Ν;

^은 Ν이고， Υ2는 Ν이고， Υ3는 CH이거나; ^ Is Ν, Υ 2 is Ν, Υ 3 is CH;

^은 Ν이고， Υ2는 CH이고, Υ3는 Ν이거나; ^ Is an Ν, Υ 2 is CH, Υ is 3 or Ν;

^은 Ν이고， Υ2는 CH이고, Υ3는 CH이거나; 또는 ^ Is Ν, Υ 2 is CH, Υ 3 is CH; or

^은 CH이고， Υ2는 CH이고， Υ3는 Ν일 수 있다. 바람직하게는， 상기 화학식 1에서， Arla 및 八 는 각각' 독립적으로， 치환 또는 비치환된 C6-20 아릴; 또는 치환 또는 비치환된 N, 0 및 로 구성되는 군으로부터 선택되는 헤테로원자를 1개 포함하는 헤테로아릴일 수 있다. 예를 들어， Arla 및 는 각각 독립적으로， 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다: ^ Is CH, Υ 2 is CH, and Υ 3 may be Ν. Preferably, in Formula 1, Ar la and八are each 'independently, a substituted or unsubstituted C 6 - 20 aryl; Or a substituted or unsubstituted N, 0 and one hetero atom selected from the group consisting of Heteroaryl. For example, Ar la and may each independently be any one selected from the group consisting of:

Figure imgf000013_0001
Figure imgf000013_0001

상기에서 ,  Above

X2는ᄋ, S , NZ4 , 또는 CZ5Z6이고， X 2 is S, NZ 4 , or CZ 5 Z 6 ,

Zi 내지 Z6은 각각 독립적으로， 수소; 중수소; 할로겐; 시아노; 니트로 ; 아미노; 치환 또는 비치환된 d-20 알킬 ; 치환 또는 비치환된 d-20 할로알킬; 치환 또는 비치환된 C6-20 아릴; 또는 치환 또는 비치환된 N, 0 및 S로 구성되는 군으로부터 선택되는 헤테로원자를 1개 이상 포함하는 헤테로아릴이고， Zi to Z 6 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-20 alkyl; Substituted or unsubstituted d-20 haloalkyl; Substituted or unsubstituted C 6 - 20 aryl; Or heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, 0 and S,

cl은 0 내지 5의 정수이고，  cl is an integer of 0 to 5,

c2는 0 내지 4의 정수이고，  c2 is an integer of 0 to 4,

c3는 0 내지 3의 ,정수이다. 이때， cl은 ^의 개수를 나타낸 것으로서, cl이 2 이상일 경우， 2 이상의 ^은 서로 동일하거나 상이할 수 있다. c2 및 c3에 대한 설명은 상기 cl에 대한 설명 및 상기 화학식의 구조를 참조하여 이해될 수 있다. 구체적으로 예를 들어， Arla 및 Arlb는 각각 독립적으로， 하기로 구성되는 군으로부터 선택되는 어느 하나일 수 있다: c3 is an integer of 0-3. At this time, cl represents the number of ^. When cl is 2 or more, two or more ^ may be the same or different from each other. Description of c2 and c3 can be understood with reference to the description of cl and the structure of the formula. Specifically, for example, Ar la and Ar lb may each independently be any one selected from the group consisting of:

Figure imgf000014_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000014_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000015_0001
Figure imgf000015_0001

Figure imgf000015_0002
또한， 상기 화학식 1에서， Ar2는 치환 또는 비치환된 C6-60 아릴이다. 이때， 아릴은 비방향족 축합환을 포함하지 않는다. 구체적으로， 치환 또는 비치환된 플루오레닐기는 본 발명의 Ar2에서 제외된다. 바람직하게는， Ar2는 비치환되거나, 또는 중수소; 할로겐; 시아노; 니트로; 아미노; 치환 또는 비치환된 d-60 알킬 ; 치환 또는 비치환된 d-60 할로알킬; Si (¾) (¾) (¾) ; C(Q4) (Q5) (Q6) 및 C6-60 아릴로 구성되는 군으로부터 각각 독립적으로 선택되는 치환기로 치환된 C6-60 아릴이고，
Figure imgf000015_0002
In addition, in Chemical Formula 1, Ar 2 is substituted or unsubstituted C 6 -60 aryl. At this time, aryl does not include a non-aromatic condensed ring. Specifically, the substituted or unsubstituted fluorenyl group is excluded from Ar 2 of the present invention. Preferably, Ar 2 is unsubstituted or deuterium; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d- 60 alkyl; Substituted or unsubstituted d-60 haloalkyl; Si (¾) (¾) (¾); 60 is an aryl, - C (Q 4) ( Q 5) (Q 6) and C 6 - C 6 substitution of from the group consisting of 60 to aryl substituents each independently selected

여기서， Qi 내지 Q6은 각각 독립적으로， 수소; 중수소; 할로겐; 시아노 ; 니트로 ; 아미노; 치환 또는 '비치환된 d-20 알킬 ; 또는 치환 또는 비치환된 C6-20 아릴일 수 있다. 예를 들어， Ar2는 하기로 구성되는 군으로부터 선택되는 어느 하나일 수있다: Here, Qi to Q 6 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or ' unsubstituted d-20 alkyl; Or substitution It may be a 20-aryl-unsubstituted C 6. For example, Ar 2 can be any one selected from the group consisting of:

Figure imgf000016_0001
Figure imgf000017_0001
Figure imgf000016_0001
Figure imgf000017_0001

상기에서，  Above

Zn 내지 Ζ14는 각각 독립적으로， 수소; 중수소; 할로겐; 시아노; 니트로 ; 아미노; 치환 또는 비치환된 d-60 알킬 ; 치환 또는 비치환된 d-eo 할로알킬; Si (¾) (¾) (¾) ; C(Q4) (¾) (¾) 및 C6-60 아릴이고， Zn to X 14 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-60 alkyl; Substituted or unsubstituted d-eo haloalkyl; Si (¾) (¾) (¾); C (Q 4 ) (¾) (¾) and C 6 -60 aryl,

여기서， ¾ 내지 ¾은 각각 독립적으로， 수소; 중수소; 할로겐; 시아노 ; 니트로 ; 아미노; 치환 또는 비치환된 d-20 알킬 ; 또는 치환 또는 비치환된 C6-20 아릴이고， Here, ¾ to ¾ are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-20 alkyl; Or a substituted or unsubstituted C 6 ring - A 20 aryl,

cll은 0 내지 5의 정수이고  cll is an integer from 0 to 5

cl2는 0 내지 7의 정수이고，.  cl2 is an integer of 0-7.

cl3는 0 내지 9의 정수이고，  cl3 is an integer of 0 to 9,

cl4는 0 내지 4의 정수이고，  cl4 is an integer of 0 to 4,

cl5는 0 내지 3의 정수이고，  cl5 is an integer of 0 to 3,

cl6은 0 내지 11의 정수이고，  cl6 is an integer from 0 to 11,

cl7은 0 내지 9의 정수이고，  cl7 is an integer of 0 to 9,

cl8은 0 내지 6의 정수이고，  cl8 is an integer from 0 to 6,

cl9는 0 내지 12의 정수이다. 이때, cll은 Zu의 개수를 나타낸 것으로서， cll이 2 이상일 경우， 2 이상의 Zu은 서로 동일하거나 상이할 수 있다. cl2 내지 cl9에 대한 설명은 상기 cll에 대한 설명 및 상기 화학식의 구조를 참조하여 이해될 수 있다. 바람직하게는， 상기에서 ¾내지 Q6은 수소; 중수소; 할로겐; 시아노; 니트로; 아미노; 메틸; 또는 페닐일 수 있다. 구체적으로 예 어， Ar2는 하기로 구성되는 군으로부터 선택되는 어느 cl9 is an integer of 0-12. In this case, cll represents the number of Z u . When cll is 2 or more, two or more Z u may be the same or different from each other. Description of cl2 to cl9 can be understood with reference to the description of the cll and the structure of the formula. Preferably, ¾ to Q 6 is hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; methyl; Or phenyl. Specifically, Ar 2 is any one selected from the group consisting of

Figure imgf000018_0001
81
Figure imgf000018_0001
81

Figure imgf000019_0001
Figure imgf000019_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000020_0001
또한， 상기 화학식 1에서， Ri 내지 ¾는 각각 독립적으로， 수소; 중수소; 시아노; 또는 치환 또는 비치환된 Cwo 알킬일 수 있다. 예를 들어， Ri 및 R2는 각각 독립적으로， 수소, 중수소， 시아노， 메틸, 또는 중수소로 치환된 메틸일 수 있고， ¾는 수소일 수 있다. 상기 화학식 1에서， nl은 의 개수를 나타낸 것으로서， nl이 2 이상일 경우， 2 이상의 ¾은 서로 동일하거나 상이할 수 있다. n2에 대한 설명은 상기 nl에 대한 설명 및 화학식 1의 구조를 참조하여 이해될 수 있다.
Figure imgf000020_0001
In addition, in Chemical Formula 1, Ri to ¾ are each independently hydrogen; heavy hydrogen; Cyano; Or substituted or unsubstituted Cwo alkyl. For example, Ri and R 2 may each independently be hydrogen, deuterium, cyano, methyl, or methyl substituted with deuterium, and ¾ may be hydrogen. In Formula 1, nl represents the number of. When nl is 2 or more, two or more ¾ may be the same or different from each other. Description of n2 may be understood with reference to the description of nl and the structure of Formula 1.

예를 들에 상기 화합물은， 하기 화합물로 구성되는 군으로부터 선택될 수 있다: oz For example, the compound may be selected from the group consisting of the following compounds: oz

Figure imgf000021_0001
Figure imgf000021_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV

Figure imgf000022_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV zz LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000022_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV zz

Figure imgf000023_0001
Figure imgf000023_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000024_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000024_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000025_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000025_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000026_0001
Figure imgf000026_0001

tLZ900/LlOZW^/13d zttnomoz OAV 9Z tLZ900 / LlOZW ^ / 13d zttnomoz OAV 9Z

Figure imgf000027_0001
Figure imgf000027_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV LZ

Figure imgf000028_0001
Figure imgf000028_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV Z LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV Z

Figure imgf000029_0001
Figure imgf000029_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 6Z LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 6Z

Figure imgf000030_0001
Figure imgf000030_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV οε LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV οε

Figure imgf000031_0001
Figure imgf000031_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000032_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000032_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000033_0001
Figure imgf000033_0001

32 32

Figure imgf000034_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000034_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000035_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000035_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000036_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000036_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000037_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000038_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000037_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000038_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000039_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 6ε
Figure imgf000039_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 6ε

Figure imgf000040_0001
Figure imgf000040_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV Of LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV Of

Figure imgf000041_0001
Figure imgf000041_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV If LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV If

Figure imgf000042_0001
Figure imgf000042_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000043_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000043_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000044_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000044_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000045_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000045_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000046_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000046_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000047_0001
Figure imgf000047_0001

 if  if

Figure imgf000048_0001
Figure imgf000048_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 8 LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 8

Figure imgf000049_0001
Figure imgf000049_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000050_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000050_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000051_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 15
Figure imgf000051_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 15

Figure imgf000052_0001
Figure imgf000052_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV Z LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV Z

Figure imgf000053_0001
Figure imgf000053_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000054_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000054_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000055_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 99
Figure imgf000055_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 99

Figure imgf000056_0001
Figure imgf000056_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000057_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000057_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000058_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 83
Figure imgf000058_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 83

Figure imgf000059_0001
Figure imgf000059_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 6S LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 6S

Figure imgf000060_0001
Figure imgf000060_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 09 LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 09

Figure imgf000061_0001
Figure imgf000061_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 19 LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 19

Figure imgf000062_0001
Figure imgf000062_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV Z9 LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV Z9

Figure imgf000063_0001
Figure imgf000063_0001

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000064_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000064_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000065_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 99
Figure imgf000065_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 99

Figure imgf000066_0001
Figure imgf000066_0001

Figure imgf000066_0002
Figure imgf000066_0003
Figure imgf000066_0002
Figure imgf000066_0003

LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000067_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000067_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000068_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000068_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000069_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000069_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000070_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000070_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000071_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000071_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000072_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000072_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000073_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000073_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV

Figure imgf000074_0001
상기 화학식 1로 표시되는 화합물은， 디벤조퓨란 또는 디벤조티오펜 코어의 특정.위치에 피리디닐기， 피리미디닐기, 또는 트리아지닐기와 같은
Figure imgf000074_0001
Compound represented by the formula (1), such as a pyridinyl group, a pyrimidinyl group, or a triazinyl group at a specific position of the dibenzofuran or dibenzothiophene core

N 원자 함유 헤테로아릴 치환기가 연결된 구조를 가지고， 디벤조퓨란 또는 디벤조티오펜 코어의 특정 위치에 방향족인 아릴 치환기가 연결됨으로써， 이를 이용한 유기 발광 소자는 플루오레닐기와 같은 비방향족 축합환기가 연결된 화합물을 이용한 유기 발광 소자에 비하여 고효율， 저 구동 전압 및 장수명 등을 나타낼 수 있다. 한편， 상기 화학식 1로 표시되는 화합물은 일례로 하기 반웅식 1과 같은 제조 방법으로 제조할 수 있다:

Figure imgf000075_0001
상기 반웅식 1에서， ， 12 , Yi 내지 Y3 , Aria , Arlb 및 Ar2 에 대한 설명은 상기 화학식 1에서 정의한 바와 같다. 상기 화학식 1로 표시되는 화합물은 상기 반웅식 1을 참고하여 제조하고자 하는 화합물의 구조에 맞추어 출발 물질을 적절히 대체하여 제조할 수 있다. 또한, 본 발명은 상기 화학식 1로 표시되는 화합물을 포함하는 유기 발광 소자를 제공한다. 일례로， 본 발명은 제 1 전극; 상기 게 1 전극과 대향하여 구비된 제 2 전극; 및 상기 게 1 전극과 상기 제 2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서， 상기 유기물 층 중 1층 이상은 상기 화학식 1로 표시되는 화합물을 포함하는， 유기 발광 소자를 제공한다. 본 발명의 유기 발광 소자의 유기물 층은 단층 구조로 이루어질 수도 있으나， 2층 이상의 유기물 층이 적층된 다층 구조로 이루어질 수 있다. 예컨대， 본 발명의 유기 발광 소자는 유기물 층으로서 정공 주입층， 정공 수송층， 발광층， 전자수송층， 전자 주입층 등을 포함하는 구조를 가질 수 있다. 그러나 유기 발광 소자의 구조는 이에 한정되지 않고 더 적은 수의 유기층을 포함할 수 있다. 구체적으로， 상기 유기물층은 발광층을 포함할 수 있고， 상기 발광층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. 이때， 상기 화학식 1로 표시되는 화합물은 발광층에서 호스트 물질로 사용될 수 있다. 또한， 본 발명에 따른 유기 발광 소자는， 기판 상에 양극， 1층 이상의 유기물 층 및 음극이 순차적으로 적층된 구조 (normal type)의 유기 발광 소자일 수 있다. 또한, 본 발명에 따른 유기 발광 소자는 기판 상에 음극， 1층 이상의 유기물 층 및 양극이 순차적으로 적층된 역방향 구조 ( inverted type)의 유기 발광 소자일 수 있다. 예컨대， 본 발명의 일실시예에 따른 유기 발광 소자의 구조는 도 1 및 2에 예시되어 있다. 도 1은 기판 ( 1)， 양극 (2)， 발광층 (3)， 음극 (4)으로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서， 상기 화학식 1로 표시되는 화합물은 상기 발광층에 포함될 수 있다. 도 2는 기판 ( 1) , 양극 (2)， 정공 주입층 (5)， 정공 수송층 (6)， 발광층 (7)， 전자수송층 (8) 및 음극 (4)로 이루어진 유기 발광 소자의 예를 도시한 것이다. 이와 같은 구조에 있어서， 상기 화학식 1로 표시되는 화합물은 상기 정공 주입층， 정공 수송층， 발광층 및 전자수송층 중 1층 이상에 포함될 수 있다. 본 발명에 따른 유기 발광 소자는， 상기 유기물 층 중 1층 이상이 상기 화학식 1로 표시되는 화합물을 포함하는 것을 제외하고는 당 기술분야에 알려져 있는 재료와 방법으로 제조될 수 있다. 또한， 상기 유기 발광 소자가 복수개의 유기물 층을 포함하는 경우， 상기 유기물 층은 동일한 물질 또는 다른 물질로 형성될 수 있다. 예컨대， 본 발명에 따른 유기 발광 소자는 기판 상에 게 1 전극， 유기물 층 및 제 2 전극을 순차적으로 적층시켜 제조할 수 있다. 이때， 스퍼터링법 (sputter ing)이나 전자빔 증발법 (e—beam evaporat ion)과 같은 PVDCphys i cal Vapor Deposi t ion)방법을 이용하여， 기판 상에 금속 또는 전도성을 가지는 금속 산화물 또는 이들의 합금을 증착시켜 양극을 형성하고， 그 위에 정공 주입층， 정공 수송층, 발광층 및 전자 수송층을 포함하는 유기물 층을 형성한 후， 그 위에 음극으로 사용할 수 있는 물질을 증착시켜 제조할 수 있다. 이와 같은 방법 외에도， 기판 상에 음극 물질부터 유기물 층， 양극 물질을 차례로 증착시켜 유기 발광 소자를 만들 수 있다. 또한 상기 화학식 1로 표시되는 화합물은 유기 발광 소자의 제조시 진공 증착법 뿐만 아니라 용액 도포법에 의하여 유기물 층으로 형성될 수 있다. 여기서， 용액 도포법이라 함은 스핀 코팅， 딥코팅, 닥터 블레이딩， 잉크젯 프린팅， 스크린 프린팅， 스프레이법， 롤 코팅 등을 의미하지만， 이들만으로 한정되는 것은 아니다. 이와 같은 방법 외에도， 기판 상에 음극 물질로부터 유기물 층 양극 물질을 차례로 증착시켜 유기 발광 소자를 제조할 수 있다 (W0 2003/012890) . 다만， 제조 방법이 이에 한정되는 것은 아니다. 일례로, 상기 제 1 전극은 양극이고， 상기 제 2 전극은 음극이거나， 또는 상기 제 1 전극은 음극이고, 상기 제 2 전극은 양극이다. 상기 양극 물질로는 통상 유기물 층으로 정공 주입이 원활할 수 있도록 일함수가 큰 물질이 바람직하다. 상기 양극 물질의 구체적인 예로는 바나듐， 크름， 구리， 아연， 금과 같은 금속 또는 이들의 합금; 아연 산화물, 인듐 산화물， 인듐주석 산화물 ( ΠΌ) , 인듐아연 산화물 ( IZ0)과 같은 금속 산화물; Ζη0:Α1 또는 SN02 : Sb와 같은 금속과 산화물의 조합; 폴리 (3- 메틸티오펜)， 폴리 [3，4- (에틸렌 -1 , 2-디옥시 )티오펜] (PED0T) , 폴리피를 및 폴리아닐린과 같은 전도성 고분자 등이 있으나， 아들에만 한정되는 것은 아니다. 상기 음극 물질로는 통상 유기물 층으로 전자 주입이 용이하도록 일함수가 작은 물질인 것이 바람직하다. 상기 음극 물질의 구체적인 예로는 마그네슘， 칼슘， 나트륨， 칼륨， 티타늄， 인듐，ᅳ 이트륨， 리튬， 가돌리늄, 알루미늄， 은， 주석 및 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 Li02/Al과 같은 다층 구조 물질 등이 있으나， 이들에만 한정되는 것은 아니다. 상기 정공 주입층은 전극으로부터 정공을 주입하는 층으로， 정공 주입 물질로는 정공을 수송하는 능력을 가져 양극에서의 정공 주입효과， 발광층 또는 발광재료에 대하여 우수한 정공 주입 효과를 갖고， 발광층에서 생성된 여기자의 전자 주입층 또는 전자주입재료에의 이동을 방지하며， 또한， 박막 형성 능력이 우수한 화합물이 바람직하다. 정공 주입 물질의 H0M0(highest occupied mol ecular orbi tal )가 양극 물질의 일함수와 주변 유기물 층의 HOMO 사이인 것이 바람직하다. 정공 주입 물질의 구체적인 예로는 금속 포피린 (porphyr in) , 올리고티오펜， 아릴아민 계열의 유기물， 핵사니트릴핵사아자트리페닐렌 계열의 유기물， 퀴나크리돈 (quinacr idone)계열의 유기물， 페릴렌 (perylene) 계열의 유기물， 안트라퀴논 및 폴리아닐린과 폴리티오펜 계열의 전도성 고분자 등이 있으나， 이들에만 한정 되는 것은 아니다. 상기 정공 수송층은 정공 주입층으로부터 정공을 수취하여 발광층까지 정공을 수송하는 층으로， 정공 수송 물질로 양극이나 정공 주입층으로부터 정공을 수송받아 발광층으로 옮겨줄 수 있는 물질로 정공에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 아릴아민 계열의 유기물， 전도성 고분자, 및 공액 부분과 비공액 부분이 함께 있는 블록 공중합체 등이 있으나, 이들에만 한정되는 것은 아니다. 상기 발광 물질로는 정공 수송층과 전자 수송층으로부터 정공과 전자를 각각 수송받아 결합시킴으로써 가시광선 영역의 빛을 낼 수 있는 물질로서， 형광이나 인광에 대한 양자 효율이 좋은 물질이 바람직하다. 구체적인 예로 8ᅳ히드록시-퀴놀린 알루미늄 착물 (Alq3) ; 카르바졸 계열 화합물; 이량체화 스티릴 (dimer i zed styryl ) 화합물; BAlq ; 10- 히드록시벤조 퀴놀린 -금속 화합물; 벤족사졸， 벤즈티아졸 및 벤즈이미다졸 계열의 화합물; 폴리 (P-페닐렌비닐렌) (PPV) 계열의 고분자; 스피로 (spi ro) 화합물; 폴리플루오렌， 루브렌 등이 있으나， 이들에만 한정되는 것은 아니다. 상기 발광충은 호스트 재료 및 도펀트 재료를 포함할 수 있다. 호스트 재료로는 상술한 화학식 1로 표시되는 화합물을 포함할 수 있다. 그 외 추가적으로， 축합 방향족환 유도체 또는 헤테로환 함유 화합물 등을 더 포함할 수 있다. 구체적으로 축합 방향족환 유도체로는 안트라센 유도체， 피렌 유도체, 나프탈렌 유도체, 펜타센 유도체 페난트렌 화합물， 플루오란텐 화합물 등이 있고， 헤테로환 함유 화합물로는 카바졸 유도체， 디벤조퓨란 유도체， 래더형 퓨란 화합물， 피리미딘 유도체 등이 있으나, 이에 한정되지 않는다. 도편트 재료로는 방향족 아민 유도체， 스트릴아민 화합물， 붕소 착체: 플루오란텐 화합물， 금속 착체 등이 있다. 구체적으로 방향족 아민 유도체로는 치환 또는 비치환된 아릴아미노기를 갖는 축합 방향족환 유도체로서， 아릴아미노기를 갖는 피렌, 안트라센， 크리센， 페리플란텐 등이 있으며， 스티릴아민 화합물로는 치환 또는 비치환된 아릴아민에 적어도 1개의 아릴비닐기가 치환되어 있는 화합물로, 아릴기， 실릴기， 알킬기， 사이클로알킬기 및 아릴아미노기로 이루어진 군에서 1 또는 2 이상 선택되는 치환기가 치환 또는 비치환된다. 구체적으로 스티릴아민.， 스티릴디아민, 스티릴트리아민， 스티릴테트라아민 등이 있으나， 이에 한정되지 않는다. 또한， 금속 착체로는 이리듐 착체， 백금 착체 등이 있으나， 이에 한정되지 않는다. 상기 전자 수송층은 전자 주입층으로부터 전자를 수취하여 발광층까지 전자를 수송하는 층으로 전자 수송 물질로는 음극으로부터 전자를 잘 주입 받아 발광층으로 옮겨줄 수 있는 물질로서， 전자에 대한 이동성이 큰 물질이 적합하다. 구체적인 예로는 8-히드록시퀴놀린의 A1 착물; Alq3를 포함한 착물; 유기 라디칼 화합물; 히드록시플라본 -금속 착물 등이 있으나, 이들에만 한정되는 것은 아니다. 전자 수송층은 종래기술에 따라 사용된 바와 같이 임의의 원하는 캐소드 물질과 함께 사용할 수 있다. 특히， 적절한 캐소드 물질의 예는 낮은 일함수를 가지고 알루미늄층 또는 실버층이 뒤따르는 통상적인 물질이다. 구체적으로 세슘， 바륨， 칼슘， 이테르붐 및 사마륨이고， 각 경우 알루미늄 층 또는 실버층이 뒤따른다. 상기 전자 주입층은 전극으로부터 전자를 주입하는 층으로， 전자를 수송하는 능력을 갖고, 음극으로부터의 전자 주입 효과， 발광층 또는 발광 재료에 대하여 우수한 전자주입 효과를 가지며， 발광층에서 생성된 여기자의 정공 주입층에의 이동을 방지하고， 또한， 박막형성능력이 우수한 화합물이 바람직하다. 구체적으로는 플루오레논， 안트라퀴노다이메탄， 다이페노퀴논， 티오피란 다이옥사이드, 옥사졸， 옥사다이아졸， 트리아졸， 이미다졸， 페릴렌테트라카복실산， 프레오레닐리덴 메탄， 안트론 등과 그들의 유도체， 금속 착체 화합물 및 질소 함유 5원환 유도체 등이 있으나， 이에 한정되지 않는다. 상기 금속 착체 화합물로서는 8-하이드록시퀴놀리나토 리튬， 비스 (8- 하이드록시퀴놀리나토)아연， 비스 (8-하이드록시퀴놀리나토)구리， 비스 (8- 하이드록시퀴놀리나토)망간， 트리스 (8-하이드록시퀴놀리나토)알루미늄， 트리스 (2-메틸 -8-하이드록시퀴놀리나토)알루미늄， 트리스 (8- 하이드록시퀴놀리나토)갈륨， 비스 (10—하이드록시벤조 [h]퀴놀리나토)베릴륨， 비스 (10-하이드록시벤조 [h]퀴놀리나토)아연 , 비스 (2-메틸 -8- 퀴놀리나토)클로로갈륨， 비스 (2-메틸 -8-퀴놀리나토) (0-크레졸라토)갈륨， 비스 (2-메틸 -8-퀴놀리나토) (1-나프를라토)알루미늄， 비스 (2-메틸 -8- 퀴놀리나토) (2-나프를라토)갈륨 등이 있으나， 이에 한정되지 않는다. 본 발명에 따른 유기 발광 소자는 사용되는 재료에 따라 전면 발광형， 후면 발광형 또는 양면 발광형일 수 있다. 또한， 상기 화학식 1로 표시되는 화합물은 유기 발광 소자 외에도 유기 태양 전지 또는 유기 트랜지스터에 포함될 수 있다. 상기 화학식 1로 표시되는 화합물 및 이를 포함하는 유기 발광 소자의 제조는 이하 실시예에서 구체적으로 설명한다. 그러나 하기 실시예는 본 발명을 예시하기 위한 것이며， 본 발명의 범위가 이들에 의하여 한정되는 것은 아니다. The N atom-containing heteroaryl substituent group has a structure in which an aromatic aryl substituent is linked to a specific position of the dibenzofuran or dibenzothiophene core, whereby the organic light emitting device using the non-aromatic condensed cyclic group such as fluorenyl group is connected. Compared with the organic light emitting device using the compound, it can exhibit high efficiency, low driving voltage and long life. On the other hand, the compound represented by the formula (1) can be prepared by a manufacturing method such as Banung Formula 1 as follows:
Figure imgf000075_0001
In Reaction Formula 1, 1 2 , Yi to Y 3 , Aria, Ar lb and Ar 2 are the same as defined in Formula 1. The compound represented by Formula 1 may be prepared by appropriately replacing the starting material in accordance with the structure of the compound to be prepared with reference to Banung Formula 1. The present invention also provides an organic light emitting device including the compound represented by Chemical Formula 1. In one embodiment, the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic layer provided between the first electrode and the second electrode, wherein at least one of the organic layers comprises a compound represented by Chemical Formula 1. to provide. The organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. For example, the organic light emitting device of the present invention may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic layer. However, the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers. Specifically, the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1. In this case, the compound represented by Chemical Formula 1 may be used as a host material in the emission layer. In addition, the organic light emitting device according to the present invention may be an organic light emitting device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate. In addition, the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. For example, the structure of an organic light emitting diode according to an embodiment of the present invention is illustrated in FIGS. 1 and 2. FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the compound represented by Formula 1 may be included in the light emitting layer. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is. In such a structure, the compound represented by Chemical Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer, and the electron transport layer. The organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1. In addition, when the organic light emitting diode includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials. For example, the organic light emitting device according to the present invention may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate. At this time, a metal or conductive metal oxide or an alloy thereof is deposited on the substrate by using a PVDC physical vapor deposition method such as sputtering or e-beam evaporat ion. After forming an anode, an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer and an electron transporting layer is formed thereon, by depositing a material that can be used as a cathode thereon. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate. In addition, the compound represented by Chemical Formula 1 may be formed as an organic layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device. Here, the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto. In addition to the above method, an organic light emitting device may be manufactured by sequentially depositing an organic material layer anode material on a substrate from a cathode material (W0 2003/012890). However, the manufacturing method is not limited thereto. In one example, the first electrode is an anode, the second electrode is a cathode, or the first electrode is a cathode, the second electrode is an anode. As the anode material, a material having a large work function is generally preferred to facilitate hole injection into the organic material layer. Specific examples of the positive electrode material include metals such as vanadium, crumb, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ΠΌ), indium zinc oxide (IZ0); Ζη0: Α1 or SN0 2 : A combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PED0T), polypyrrole and polyaniline, but are not limited to sons no. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer. Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or Li0 2 / Al, and the like, but are not limited thereto. The hole injection layer is a layer for injecting holes from the electrode, the hole injection material has the ability to transport holes to have a hole injection effect at the anode, has an excellent hole injection effect to the light emitting layer or the light emitting material, The compound which prevents the excitons from moving to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable. Preferably, the highest occupied mol ecular orbital (HO) of the hole injection material is between the work function of the anode material and the HOMO of the surrounding organic layer. Specific examples of the hole injection material include metal porphyr (in), oligothiophene, arylamine-based organics, nucleonitrile-nucleated azatriphenylene-based organics, quinacridone-based organics, and perylene ) Organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto. The hole transport layer receives holes from the hole injection layer As a layer for transporting holes to the light emitting layer, a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer as a hole transporting material is suitable. Specific examples include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion, but are not limited thereto. The light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable. Concrete examples thereof include 8′-hydroxy quinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimer i zed styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Polymers of the poly (P-phenylenevinylene) (PPV) family; Spi ro compounds; Polyfluorene, rubrene and the like, but are not limited thereto. The light emitting insect may include a host material and a dopant material. The host material may include a compound represented by Chemical Formula 1 described above. In addition, it may further include a condensed aromatic ring derivative or a hetero ring-containing compound. Specifically, the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds, and the heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives and ladder type furans. Compounds, pyrimidine derivatives, and the like, but is not limited thereto. Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes : fluoranthene compounds, metal complexes, and the like. Specifically, the aromatic amine derivatives are condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene and periplanthene having an arylamino group, and the styrylamine compound may be substituted or unsubstituted. To arylamine As a compound in which at least one arylvinyl group is substituted, a substituent selected from one or two or more selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specifically, styryl amine, styryl diamine, styryl triamine, styryl tetraamine and the like, but is not limited thereto. In addition, the metal complex includes an iridium complex, a platinum complex, and the like, but is not limited thereto. The electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer. As an electron transport material, a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is suitable. Do. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto. The electron transport layer can be used with any desired cathode material as used in accordance with the prior art. In particular, examples of suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, etherboom and samarium, each followed by an aluminum or silver layer. The electron injection layer is a layer for injecting electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from the cathode, has an excellent electron injection effect to the light emitting layer or the light emitting material, and hole injection of excitons generated in the light emitting layer The compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable. Specifically, fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the derivatives thereof, metal Complex compounds and nitrogen-containing five-membered ring derivatives; and the like, but are not limited thereto. Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Manganese, tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis ( 10—hydroxybenzo [h] quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl -8-quinolinato) (0-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphlato) aluminum, bis (2-methyl-8-quinolinato) (2 -Naphlato) gallium, etc., but is not limited thereto. The organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used. In addition, the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device. Preparation of the compound represented by Chemical Formula 1 and an organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.

Figure imgf000081_0001
Figure imgf000081_0001

브로모 -3-플루오로 -2-요오드벤젠 ( l-bromo-3-fluoro-2- iodobenzene)(100 g, 333.5 mmol), 5-클로로 -2-메톡시페닐보론산 ((5- chloro-2-methoxyphenyl )boronic acid)(62.2 g, 333.5 mmol)를 테트라하이드로퓨란 (THF)800 ml에 녹였다. 여기에 탄산나트륨 (Na2C03) 2 M 용액 (500 mL), 테트라키스 (트리페닐포스핀)팔라듐 (0) [Pd(PPh3)4](7.7 g, 6.7 隱 ol)을 넣고 12 시간 환류시켰다. 반웅이 끝난 후 상온으로 넁각시키고, 생성된 흔합물을 물과 를루엔으로 3회 추출하였다. 를루엔층을 분리한 뒤 황산마그네슘 (magnesium sulfate)으로 건조하여 여과한 여액을 감압증류하여 얻은 흔합물을 클로로품， 에탄올을 이용해 3희 재결정 하여 화합물 P-K53.7 g, 수율 51 %;MS:[M+H]+=314)을 얻었다. L-bromo-3-fluoro-2-iodobenzene (100 g, 333.5 mmol), 5-chloro-2-methoxyphenylboronic acid ((5-chloro- 2-methoxyphenyl) boronic acid) (62.2 g, 333.5 mmol) was dissolved in 800 ml of tetrahydrofuran (THF). This was followed by sodium carbonate (Na 2 CO 3 ) 2 M solution (500 mL), tetrakis (triphenylphosphine) palladium (0) [Pd (PPh 3 ) 4 ] (7.7 g, 6.7 μl) was added and refluxed for 12 hours. After the reaction was finished, the mixture was cooled to room temperature, and the resultant mixture was extracted three times with water and toluene. The toluene layer was separated and dried over magnesium sulfate, and the filtrate was filtered and distilled under reduced pressure. The mixture was recrystallized from chloroform and ethanol for 3 times to obtain compound P-K53.7 g, yield 51%; MS; : [M + H] + = 314).

Figure imgf000082_0001
Figure imgf000082_0001

P-1 P-2  P-1 P-2

화합물 P-l(50.0 g, 158.5 醒 ol)을 디클로로메탄 (Dichlorometahne)(600 ml)에 녹인 뒤 0°C로 넁각시킨다. 보론트리브로마이드 (boron tr ibromide)(15.8 ml , 166.4 mmol)를 천천히 적가한 뒤 12시간동안 교반하였다. 반웅이 종료된 후 물로 3회 세척하고， 황산마그네슘 (magnesium sulfate)으로 건조하여 여과한 여액을 감압증류하고 컬럼크로마토크래피로 정제하여 화합물 P-2(47.4 g, 수율 99 %;MS:[M+H]+=300)을 얻었다. Compound Pl (50.0 g, 158.5 μl) is dissolved in Dichlorometahne (600 ml) and then cooled to 0 ° C. Boron tribromide (boron tr ibromide) (15.8 ml, 166.4 mmol) was slowly added dropwise and stirred for 12 hours. After the reaction was completed, the mixture was washed three times with water, dried over magnesium sulfate, and the filtrate was filtered under reduced pressure and purified by column chromatography. Compound P-2 (47.4 g, yield 99%; MS: [M + H] + = 300).

Figure imgf000082_0002
Figure imgf000082_0002

P-2 P-3  P-2 P-3

화합물 P-2 0.0 g, 132.7 mmol)을 증류된 다이메틸뇨름아마이드 (DMF) (400ml)에 녹인다. 이를 0°C로 넁각시키고， 여기에 나트륨 하이드리드 (sodium hydride) (3.5 g, 145.9 mmol) 를 천천히 적가하였다. 20분동안 교반한 뒤 10CTC에서 1시간동안 교반하였다. 반옹이 종료된 후 상온으로 넁각하고， 에탄올 (Ethanol) 100 ml을 천천히 넣었다. 위 흔합물을 감압증류 하여 얻은 흔합물을 클로로포름， 에틸아세테이트로 재결정하여 화합물 P-3(30.3 g, 수율 81 %;MS:[M+H]+=280)을 얻었다.

Figure imgf000083_0001
0.0 g, 132.7 mmol) of compound P-2 are dissolved in distilled dimethylurimamide (DMF) (400 ml). It was angled to 0 ° C., and sodium hydride (3.5 g, 145.9 mmol) was slowly added dropwise thereto. After stirring for 20 minutes, the mixture was stirred at 10 CTC for 1 hour. After the reaction was completed, the mixture was cooled to room temperature, and 100 ml of ethanol was slowly added thereto. The mixture obtained by distillation under reduced pressure of the above mixture was recrystallized with chloroform and ethyl acetate to obtain compound P-3 (30.3 g, yield 81%; MS: [M + H] + = 280).
Figure imgf000083_0001

P'3 P-4  P'3 P-4

화합물 P-3(30.0 g, 106.6 隱 ol)을 테트라하이드로퓨란 (300 ml)에 녹인 후， 78°C로 온도를 낮추고 1.7 M 터셔리-부틸리튬 (t-BuLi)(62.7 ml, 106.6 誦 ol)을 천천히 가하였다. 동일 온도에서 한 시간 동안 교반한 후 트리아이소프로필보레이트 (B(0iPr)3)(28.3 ml, 213.1 醒 ol)을 가하고, 상온으로 은도를 서서히 올리면서 3시간동안 교반하였다. 반응 흔합물에 2 N 염산수용액 (200 ml)을 가하고 1.5 시간 동안 상온에서 교반하였다. 생성된 침전물을 거르고 물과 에틸에테르 (ethyl ether)로 차례로 씻은 후 진공 건조하였다. 건조후 에틸에테르에 분산시켜 두 시간 동안 교반한 후 여과하고 건조하여 화합물 P-4(24.4 g, 수율 93 ； MS:[M+H]+=247)을 제조하였다. Dissolve compound P-3 (30.0 g, 106.6 μl) in tetrahydrofuran (300 ml), lower the temperature to 78 ° C. and 1.7 M tert-butyllithium (t-BuLi) (62.7 ml, 106.6 μl ol). ) Was added slowly. After stirring for one hour at the same temperature, triisopropylborate (B (0iPr) 3 ) (28.3 ml, 213.1 醒 ol) was added, and the mixture was stirred for 3 hours while gradually raising the silver to room temperature. 2N aqueous hydrochloric acid solution (200 ml) was added to the reaction mixture, which was stirred for 1.5 hours at room temperature. The resulting precipitate was filtered off, washed sequentially with water and ethyl ether, and dried in vacuo. After drying, the mixture was dispersed in ethyl ether, stirred for 2 hours, filtered, and dried to prepare compound P-4 (24.4 g, yield 93; MS: [M + H] + = 247).

Figure imgf000083_0002
Figure imgf000083_0002

P-4 P-5 화합물 P-4(20.0 g, 81.2 mmol)과 2-chloro-4,6_diphenyl-l,3,5- triazine(21.8 g, 81.2 匪 ol)을 테트라하이드로퓨란 (250 ml)에 분산시킨 후， 2M 탄산칼륨수용액 (aq. K2C03)(33.6 ml, 243.5 醒 ol)을 첨가하고 테트라키스트리페닐포스피노팔라듐 [Pd(PPh3)4](1.9 g, 2 mol%)을 넣은 후 4시간 동안 교반 환류하였다. 상온으로 온도를 낮추고 생성된 고체를 여과하였다ᅳ 여과된 고체를 테트라하이드로퓨란과 에틸아세테이트로 재결정하고 여과한 뒤， 건조하여 화합물 P-5(32.4 g, 수율 92 %; MS:[M+H]+=434)를 제조하였다. P-4 P-5 Compound P-4 (20.0 g, 81.2 mmol) and 2-chloro-4,6_diphenyl-l, 3,5-triazine (21.8 g, 81.2 匪 ol) were added to tetrahydrofuran (250 ml). After dispersion, 2M aqueous potassium carbonate (aq. K 2 C0 3 ) (33.6 ml, 243.5 醒 ol) was added and tetrakistriphenylphosphinopalladium [Pd (PPh 3 ) 4 ] (1.9 g, 2 mol%) After stirring, the mixture was refluxed for 4 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered and dried to give the compound P-5 (32.4 g, yield 92%; MS: [M + H] + = 434).

Figure imgf000084_0001
Figure imgf000084_0001

화합물 P-5(30 g, 69.2 隱 ol) 비스 (피나콜라토)디보론 (Bis(pinacolato)diborone)(19.3 g, 76.1 mmol) 포타슘아세테이트 (potassium acetate) (20.4 g, 207.5 mmol), 테트라키스트리페닐포스피노팔라듐 (0) [Pd(PPh3)4](1.6 g, 2 η )1¾)을 테트라하이드로퓨란 (300 ml) 에 넣고 12시간 동안 환류시켰다. 반웅이 종료된 후 상온으로 식힌 뒤 감압 증류하여 용매를 제거하였다. 이것을 클로로포름 (Chloroform)에 녹이고 물로 3회 씻어낸 뒤 유기층을 분리하여 황산 마그네슘 (Magnesium sulfate)으로 건조하였다. 이를 감압 증류하여 화합물 P-6(34.5 g, 수율 95 %； MS: [M+H]+=526)을 제조하였다. Compound P-5 (30 g, 69.2 隱 ol) bis (pinacolato) diborone (19.3 g, 76.1 mmol) potassium acetate (20.4 g, 207.5 mmol), tetrakis Triphenylphosphinopalladium (0) [Pd (PPh 3 ) 4 ] (1.6 g, 2 η) 1¾) was added to tetrahydrofuran (300 ml) and refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and then distilled under reduced pressure to remove the solvent. This was dissolved in chloroform, washed three times with water, and then the organic layer was separated and dried over magnesium sulfate. This was distilled under reduced pressure to obtain compound P-6 (34.5 g, yield 95%; MS: [M + H] + = 526).

Figure imgf000084_0002
Figure imgf000084_0002

화합물 P-6(20.0 g, 38.1 mmol)과 2-브로모페난트렌 (2- bromophenanthrene)(9.8 g, 38.1 mmol)을 테트라하이드로퓨란 (250 ml)에 분산시킨 후, 2M 탄산칼륨수용액 (aq. K2C03)(57.2 ml, 114.3 mmol)을 첨가하고 테트라키스트리페닐포스피노팔라듐 [Pd(PPh3)4](1.4 g, 2 mol%)을 넣은 후 5시간 동안 교반 환류하였다. 상온으로 온도를 낮추고 생성된 고체를 여과하였다. 여과된 고체를 클로로포름과 에틸아세테이트로 재결정하고 여과한 뒤， 건조하여 화합물 1(17.8 g, 수율 81 %； MS:[M+H]+=576)을 제조하였다. Compound P-6 (20.0 g, 38.1 mmol) and 2-bromophenanthrene (9.8 g, 38.1 mmol) were dispersed in tetrahydrofuran (250 ml), followed by 2M aqueous potassium carbonate solution (aq. K 2 CO 3 ) (57.2 ml, 114.3 mmol) Tetrakistriphenylphosphinopalladium [Pd (PPh 3 ) 4 ] (1.4 g, 2 mol%) was added thereto, followed by stirring under reflux for 5 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized with chloroform and ethyl acetate, filtered and dried to give compound 1 (17.8 g, yield 81%; MS: [M + H] + = 576).

Figure imgf000085_0001
Figure imgf000085_0001

2-브로모페난트렌 (2-bromophenanthrene) 대신 9-브로모페난트렌 (9- bromophenanthrene)(9.8 g, 38.1 mmol)를 사용한 것 외에는 합성예 1—1과 동일한 방법으로 화합물 2(18.4g, 수율 84 ； MS:[M+H]+=576) 을 제조하였다. Compound 2 (18.4 g, yield) in the same manner as in Synthesis Example 1-1 except that 9-bromophenanthrene (9.8 g, 38.1 mmol) was used instead of 2-bromophenanthrene 84; MS: [M + H] + = 576).

Figure imgf000085_0002
Figure imgf000085_0002

2-브로모페난트렌 (2-bromophenanthrene ) 대신  Instead of 2-bromophenanthrene

페닐나프탈렌 (l-brotno-4-phenylnaphthalene)(10.8 g, 38 Phenylnaphthalene (l-brotno-4-phenylnaphthalene) (10.8 g, 38

것 외에는 합성예 1-1과 동일한 방법으로 화합물 3(18 Compound 3 (18) in the same manner as in Synthesis example 1-1 except for

MS:[M+H]+=602) 을 제조하였다.

Figure imgf000086_0001
MS: [M + H] + = 602).
Figure imgf000086_0001

P-6  P-6

2-브로모페난트렌 (2-bromophenanthrene) 대신 2-브로모트리페닐렌 (2- bromotriphenylene)(11.7 g, 38.1 mmol)를 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 4(2ᄂ0 g, 수율 88 %； MS:[M+H]+=626) 을 제조하였다. Compound 4 (2b0) in the same manner as in Synthesis Example 1-1, except that 2-bromotriphenylene (11.7 g, 38.1 mmol) was used instead of 2-bromophenanthrene. g, yield 88%; MS: [M + H] + = 626).

Figure imgf000086_0002
Figure imgf000086_0002

2-브로모페난트렌 (2-bromophenanthrene) 대신 9-(4- 브로모페닐)페난트렌(9-(4ᅳ13 厦)1)1 1^1)1)1 11£1 11^1 )(12.7 g, 38.1 mmol)를 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 11(19.9 g, 수율 80 %； MS:[M+H]+=652) 을 제조하였다. 합성예 1-6: 화합물 12의 제조 9- (4-bromophenyl) phenanthrene (9- (4 ᅳ 13 厦) 1) 1 1 ^ 1) 1) 1 11 £ 1 11 ^ 1) instead of 2-bromophenanthrene Compound 11 (19.9 g, yield 80%; MS: [M + H] + = 652) was prepared in the same manner as in Synthesis Example 1-1 except that 12.7 g, 38.1 mmol) was used. Synthesis Example 1-6 Preparation of Compound 12

Figure imgf000087_0001
Figure imgf000087_0001

il합물 12  il compound 12

2-브로모페난트렌 (2-bromophenanthrene) 대신 9-(2_브로모 -[1， 1'- 바이페닐] -2-일)페난트렌 (9-(21 -bromo- [1,1' -bi phenyl ] _2— 9- (2_bromo- [1,1'-biphenyl] -2-yl) phenanthrene (9- (2 1 -bromo- [1,1 ') instead of 2-bromophenanthrene -bi phenyl] _2—

yl)phenanthrene)(15.6 g, 38.1 mmol)를 사용한 것 외에는 합성예 1—1과 동일한 방법으로 화합물 12(22.5 g, 수율 81 ； MS:[M+H]+=728) 을 제조하였다. Compound 12 (22.5 g, yield 81; MS: [M + H] + = 728) was prepared in the same manner as in Synthesis Example 1-1 except that yl) phenanthrene) (15.6 g, 38.1 mmol) was used.

Figure imgf000087_0002
Figure imgf000087_0002

2-브로모페난트렌 (2-bromophenanthrene) 대신 7_(4-브로모페닐) -10- 페닐플로란텐 (7-(4-bromophenyl)— 10— phenylf luoranthene)(16.5 g, 38.1 隱 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 13(21.8 g, 수율 76 %; MS:[M+H]+=752) 을 제조하였다. 합성예 1-8: 화합물 25의 제조 7- (4-bromophenyl) -10-phenylfloanthene (10-phenylf luoranthene) (16.5 g, 38.1 隱 ol) instead of 2-bromophenanthrene A compound 13 (21.8 g, yield 76%; MS: [M + H] + = 752) was prepared in the same manner as in Synthesis Example 1-1 except for use. Synthesis Example 1-8: Preparation of Compound 25

Figure imgf000088_0001
Figure imgf000088_0001

- 25  -25

2-브로모페난트렌 (2-bromophenanthr ene ) 대신 ( (4- 브로모페닐)메탄트리일)트리벤젠 (( (4- bromophenyl )methanetriyl )tribenzene)(15.2 g, 38.1 隱 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 25(24.3 g, 수율 89 MS:[M+H]+=718) 을 제조하였다. Except for using ((4-bromophenyl) methanetriyl) tribenzene (((4-bromophenyl) methanetriyl) tribenzene) (15.2 g, 38.1 隱 ol) instead of 2-bromophenanthrene Compound 25 (24.3 g, yield 89 MS: [M + H] + = 718) was prepared in the same manner as in Synthesis example 1-1.

Figure imgf000088_0002
Figure imgf000088_0002

2-브로모페난트렌 (2-bromophenanthrene) 대신 4-브로모 -1,1' :3'，1 터페닐 (4-bromo-l,l' :3' ,1' '-terpheny 1)(11.8 g, 38.1 mmol)을 사용한 외에는 합성예 1-1과 동일한 방법으로 화합물 26(19.9 g, 수율 83 MS:[M+H]+=628) 을 제조하였다. 합성예 1-10: 화합물 28의 제조 4-bromo-1,1 ': 3', 1 terphenyl (4-bromo-l, l ': 3', 1 '' -terpheny 1) instead of 2-bromophenanthrene (11.8 Compound 26 (19.9 g, yield 83 MS: [M + H] + = 628) was prepared in the same manner as in Synthesis Example 1-1 except for using g, 38.1 mmol). Synthesis Example 1-10: Preparation of Compound 28

Figure imgf000089_0001
Figure imgf000089_0001

2-브로모페난트렌 (2-bromophenanthrene) 대신 4-브로모 -5 '―페닐- 1,1' :3' ,1' '-터페닐 (4-bromo-5' -phenyl L,l'：3' ,1' ' -ter phenyl ) (14.7 g, 38.1 隱 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 28(21.7 g, 수율 81 %； MS:[M+H]+=704) 을 제조하였다. 4-bromo-5'-phenyl-1,1 ': 3', 1'-terphenyl (4-bromo-5'-phenyl L, l) instead of 2-bromophenanthrene: Compound 28 (21.7 g, yield 81%; MS: [M + H] + = in the same manner as in Synthesis Example 1-1 except for using 3 ', 1''-ter phenyl) (14.7 g, 38.1 隱 ol) 704) was prepared.

Figure imgf000089_0002
Figure imgf000089_0002

2-브로모페난트렌 (2-bromophenanthrene) 대신 4'' '-브로모- 1,1'：3',1' ' :4' '，1' ' '-쿼터페닐 (4' ' '-bromo-1,1'：3'，1' '：4' 1，1' ' '― quaterphenyl)(14.7 g, 38.1 隱 ol)을 사용한 것 외에는 합성예 1—1과 동일한 방법으로 화합물 46(22.3 g, 수율 83 ； MS: [M+H]+=704) 을 제조하였다. 합성예 1-12: 화합물 55의 제초 4 '''-bromo-1,1': 3 ', 1'':4'',1''' -quaterphenyl (4 '''-bromo instead of 2-bromophenanthrene) Compound 46 (22.3 g) in the same manner as in Synthesis Example 1-1, except that -1,1 ': 3', 1 '': 4 ' 1 , 1''' -quaterphenyl) (14.7 g, 38.1 隱 ol) was used. , Yield 83; MS: [M + H] + = 704) was prepared. Synthesis Example 1-12: Herbicide of Compound 55

Figure imgf000090_0001
Figure imgf000090_0001

P-6 화합울 55  P-6 Harmony Wool 55

2-브로모페난트렌 (2-bromophenanthrene) 대신 3-브로모 -1， 1' :4'， 1' '- 터페닐 (3-brom으 1，1' :4' ,1' '-terphenyl)(11.8 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 55(20.6 g, 수율 86 ； MS:[M+H]+= 628) 을 제조하였다. -13: 화합물 57의 제조 3-bromo-1, 1 ': 4', 1 '' -terphenyl (3-brom 1，1 ': 4', 1 '' -terphenyl) instead of 2-bromophenanthrene Compound 55 (20.6 g, yield 86; MS: [M + H] + = 628) was prepared in the same manner as in Synthesis Example 1-1 except that (11.8 g, 38.1 mmol) was used. -13: preparation of compound 57

Figure imgf000090_0002
Figure imgf000090_0002

2-브로모페난트렌 (2-bromophenanthrene) 대신 9-(3- 브로모페닐)페난트렌 (9-(3-bromophenyl)phenanthrene)(12.7 g, 38.1 mmol)를 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 57(20.4 g, 수율 82 ； MS:[M+H]+=652) 을 제조하였다. 합성예 1-14: 화합물 62의 제조 Synthesis Example 1-1 except that 9- (3-bromophenyl) phenanthrene (12.7 g, 38.1 mmol) was used instead of 2-bromophenanthrene. Compound 57 (20.4 g, yield 82; MS: [M + H] + = 652) was prepared in the same manner. Synthesis Example 1-14: Preparation of Compound 62

Figure imgf000091_0001
Figure imgf000091_0001

2-브로모페난트렌 (2-bromophenanthrene) 대신 3-브로모 5'—페닐- 1，1'：3',1' '―터페닐^-！ ^ 으^- 니1 :3'，1' '-terphenyl)(14.7 g, 38.1 匪 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 62(22.3 g, 수율 83 %; MS: [M+H]+=704) 을 제조하였다. 3-bromo 5'-phenyl-1,1 ': 3', 1 '' -terphenyl ^-！ ^ Eh-ni 1 : 3 '， 1' instead of 2-bromophenanthrene Compound 62 (22.3 g, yield 83%; MS: [M + H] + = 704) was prepared in the same manner as in Synthesis Example 1-1 except for using '-terphenyl) (14.7 g, 38.1 μl ol).

Figure imgf000091_0002
Figure imgf000091_0002

화합을 65  Unity 65

2-브로모페난트렌 (2— broniophenanthrene) 대신 5'-브로모- 1,1' :3' ,1' '：3' ' ,1' 1 '-쿼터페닐 (5'— bromo— 1，1'：3',1' '：3' ' ,1' 1 '― 5'-bromo- 1,1 ': 3', 1 '' ： 3 '', 1 ' 1 ' -quaterphenyl (2'-bromo— 1，1 instead of 2-bromophenanthrene '： 3', 1 '' ： 3 '', 1 ' 1 ' ―

quaterphenyl)(14.7 g, 38.1 醒 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 65(21.7 g, 수율 81 %; MS:[M+H]+=704) 을 제조하였다. 합성예 1-16: 화합물 66의 제조 A compound 65 (21.7 g, Yield 81%; MS: [M + H] + = 704) was prepared in the same manner as in Synthesis Example 1-1 except that quaterphenyl) (14.7 g, 38.1 μl ol) was used. Synthesis Example 1-16 Preparation of Compound 66

Figure imgf000092_0001
Figure imgf000092_0001

화합물 66  Compound 66

2-브로모페난트렌 (2-bromophenanthrene) 대신 2—브로모- 2—bromo- instead of 2-bromophenanthrene

1,1'：3',1' ' :3' ' ,1' 1 '-쿼터페닐 (2-bromo-l,l'：3',1' '：3' ' 1' 1 '― 1,1 '： 3', 1 '': 3 '', 1 ' 1 ' -Quarterphenyl (2-bromo-l, l '： 3', 1 '' ： 3 '' 1 ' 1 ' ―

quaterphenyl)(14.7 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 66(20.6 g, 수율 77 %; MS:[M+H]+=704) 을 제조하였다. Compound 66 (20.6 g, yield 77%; MS: [M + H] + = 704) was prepared in the same manner as in Synthesis Example 1-1 except that quaterphenyl) (14.7 g, 38.1 mmol) was used.

Figure imgf000092_0002
Figure imgf000092_0002

화합을樹  Unity

2-브로모페난트렌 (2-bromophenanthrene) 대신 4,4' ,4' '-((4- 브로모페닐)메탄트리일)트리스 (메틸벤젠) (44' ,4' '-((4- bromopheny 1 )methanet r iy 1 ) t r i s (methyl benzene) ) ( 16.9 g, 38.1 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 68(22.9 g, 수율 79 %； MS:[M+H]+=760) 을 제조하였다.

Figure imgf000093_0001
4,4 ', 4''-((4-bromophenyl) methanetriyl) tris (methylbenzene) (44', 4 ''-((4- instead of 2-bromophenanthrene) Compound 68 (22.9 g, yield 79%; MS: [M + H] in the same manner as in Synthesis Example 1-1 except for using bromopheny 1) methanet r iy 1) tris (methyl benzene)) (16.9 g, 38.1 ol) ] + = 760).
Figure imgf000093_0001

2—브로모페난트렌 (2— bromophenanthrene) 대신 5 '-(4-브로모페닐) )― 1,1'：3',1' '-터페닐 -2,2' '，3,3' '，4，4' '，5，5' '，6，6' '—디 10  2—bromophenanthrene instead of 2—bromophenanthrene—1,1 ': 3', 1'-terphenyl-2,2 ', 3,3' ， 4，4 '' ， 5，5 '' ， 6，6 '' —D 10

( 5 ' - ( 4-br omopheny 1 )-1,1' :3' , 1 ' '—terphenyl—  (5 '-(4-br omopheny 1) -1,1': 3 ', 1' '—terphenyl—

2,2" ,3,3" ,4,4' 1 ,5,5" ,6,6' '-dl0)(15.1 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 72(20.7 g, 수율 76 %; MS:[M+H]+=714) 을 제조하였다. Compound in the same manner as in Synthesis Example 1-1 except for using 2,2 ", 3,3", 4,4 ' 1 , 5,5 ", 6,6'-dl0) (15.1 g, 38.1 mmol). 72 (20.7 g, yield 76%; MS: [M + H] + = 714) was prepared.

Figure imgf000093_0002
Figure imgf000093_0002

합물 81  Compound 81

2-브로모페난트렌 (2-bromophenanthrene) 대신 3—(3_ 브로모페닐)페난트렌 (3-(3-bromophenyl)phenanthrene)(12.7 g, 38.1 隱 ol)를 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 81(18.9 g, 수율 76 %； MS:[M+H]+=652) 을 제조하였다. -20: 화합물 59의 제조 Synthesis Example 1-1 except that 3- (3-bromophenyl) phenanthrene (12.7 g, 38.1 隱 ol) was used instead of 2-bromophenanthrene Compound 81 (18.9 g, yield 76%; MS: [M + H] + = 652) was prepared in the same manner. -20: preparation of compound 59

Figure imgf000094_0001
Figure imgf000094_0001

2-브로모페난트렌 (2— bromophenanthrene) 대신 2-(3- 브로모페닐)트리페닐렌 (3-(2-(3-bromophenyl)triphenylene)(14.6 g, 38.1 匪 ol)를 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 59(19.5 g, 수율 73 %； MS:[M+H]+=702) 을 제조하였다. Synthesis except using 2- (3-bromophenyl) triphenylene (14.6 g, 38.1 匪 ol) instead of 2-bromophenanthrene Compound 59 (19.5 g, yield 73%; MS: [M + H] + = 702) was prepared in the same manner as in Example 1-1.

Figure imgf000094_0002
Figure imgf000094_0002

2—브로모페난트렌 (2-bromophenanthrene) 대신 5'-브로모- 2—5'-bromo- instead of 2-bromophenanthrene

1，1' :3'，1' '-터페닐 (5'— bromo-1,1' :3' ,1' '― terphenyl)(11.8 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 45(19.4 g, 수율 81 %; MS:[M+H]+= 628) 을 제조하였다. 합성예 1-22: 화합물 54의 제조 Synthesis Example 1-1, except that 1,1 ': 3', 1 ''-terphenyl (5'—bromo-1,1 ': 3', 1 '' -terphenyl) (11.8 g, 38.1 mmol) was used. Compound 45 (19.4 g, yield 81%; MS: [M + H] + = 628) was prepared in the same manner as the above. Synthesis Example 1-22: Preparation of Compound 54

Figure imgf000095_0001
Figure imgf000095_0001

2-브로모페난트렌 (2-bromophenanthrene) 대신 5'-브로모- 5'-bromo- instead of 2-bromophenanthrene

1,1'：3',1' '：4' ',Ι' ' '-쿼터페닐 (5'-bromo-l,l' :3'，1' ' :4' '，1' ' '- quaterphenyl)(14.7 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 54(21.2 g, 수율 79 %； MS:[M+H]+=704) 을 제조하였다. 1,1 '： 3', 1 '' ： 4 '', Ι '''-Quarterphenyl(5'-bromo-l,l': 3 '， 1'':4''，1'''- Compound 54 (21.2 g, yield 79%; MS: [M + H] + = 704) was prepared in the same manner as in Synthesis Example 1-1 except that quaterphenyl) (14.7 g, 38.1 mmol) was used.

Figure imgf000095_0002
Figure imgf000095_0002

화합울 29  Harmony Wool 29

2—브로모페난트렌 (2-bromophenanthrene) 대신 2-브로모 -1，1'- 비페닐 (2-bromo-l,l'-biphenyl)(8.9 g, 38.1 圆 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 29(15.6 g, 수율 74 ； MS: [M+H]+=552) 을 제조하였다. 합성예 2: 중간체 화합물 P-8의 제조 Synthesis example except that 2-bromo-1,1'-biphenyl (8.9 g, 38.1 圆 ol) was used instead of 2-bromophenanthrene Compound 29 (15.6 g, yield 74; MS: [M + H] + = 552) was prepared in the same manner as in 1-1. Synthesis Example 2 Preparation of Intermediate Compound P-8

Figure imgf000096_0001
Figure imgf000096_0001

P-4 P-7  P-4 P-7

화합물 P-4(40.0 g, 162.3 mmol)과 2-([l,l'-biphenyl]-4-yl)-4- ch 1 or ο-6-pheny l-l,3,5-triazine(55.8 g, 162.3 mmol)을 테트라하이드로퓨란 (500 ml)에 분산시킨 후, 2M 탄산칼륨수용액 (aq. K2C03)(67.2 ml, 486.9 隱 ol)을 첨가하고 테트라키스트리페닐포스피노팔라듐 [Pd(PPh3)4](3.8 g, 2 ηω1¾)을 넣은 후 4시간 동안 교반 환류하였다. 상온으로 온도를 낮추고 생성된 고체를 여과하였다ᅳ 여과된 고체를 테트라하이드로퓨란과 에틸아세테이트로 재결정하고 여과한 뒤， 건조하여 화합물 P-7(73.7 g, 수율 89 %; MS:[M+H Compound P-4 (40.0 g, 162.3 mmol) and 2-([l, l'-biphenyl] -4-yl) -4- ch 1 or ο-6-pheny ll, 3,5-triazine (55.8 g, 162.3 mmol) is dispersed in tetrahydrofuran (500 ml), and then 2M aqueous potassium carbonate solution (aq.K 2 CO 3 ) (67.2 ml, 486.9 μl) is added and tetrakistriphenylphosphinopalladium [Pd (PPh 3 ) 4 ] (3.8 g, 2 ηω 1¾) was added and stirred under reflux for 4 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered and dried to obtain compound P-7 (73.7 g, yield 89%; MS: [M + H).

Figure imgf000096_0002
Figure imgf000096_0002

비스 (피나콜라토)디보론 (Bis(pinacolato)diborone)(38.6 g, 152.13 mmol) 포타슴아세테이트 (potassium acetate)(40.7 g, 414.9 mmol) , 테트라키스트리페닐포스피노팔라듐 (0) [Pd(PPh3)4](3.2 g, 2 mol%)을 테트라하이드로퓨란 (600 ml) 에 넣고 12시간 동안 환류시켰다. 반응이 종료된 후 상온으로 식힌 뒤 감압 증류하여 용매를 제거하였다. 이것을 클로로포름 (Chloroform)에 녹이고 물로 3회 씻어낸 뒤 유기층을 분리하여 황산 마그네슴 (Magnesium sulfate)으로 건조하였다. 이를 감압 증류하여 화합물 P-8(75.7 g, 수율 91 %； MS:[M+H]+=602)을 제조하였다. Bis (pinacolato) diborone (38.6 g, 152.13 mmol) potassium acetate (40.7 g, 414.9 mmol), tetrakistriphenylphosphinopalladium (0) [Pd ( PPh 3 ) 4 ] (3.2 g, 2 mol%) was added to tetrahydrofuran (600 ml) and refluxed for 12 hours. Reaction After completion of cooling to room temperature and distillation under reduced pressure to remove the solvent. This was dissolved in chloroform, washed three times with water, and the organic layer was separated and dried over magnesium sulfate. This was distilled under reduced pressure to obtain compound P-8 (75.7 g, yield 91%; MS: [M + H] + = 602).

Figure imgf000097_0001
Figure imgf000097_0001

P-8  P-8

화합물 P-6 대신 화합물 P-8(22.9 g, 38.1 画 ol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-(3-브로모페닐)나프탈렌 (2- (3-bromopheny 1 )naphthal ene) ( 10.8 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 9(19.9 g, 수율 77 ； MS:[M+H]+= 678) 을 제조하였다. Compound P-8 (22.9 g, 38.1 画 ol) instead of compound P-6, 2- (3-bromophenyl) naphthalene instead of 2-bromophenanthrene (2- (3-bromopheny 1) naphthal Compound 9 (19.9 g, yield 77; MS: [M + H] + = 678) was prepared in the same manner as in Synthesis Example 1-1, except that ene) (10.8 g, 38.1 mmol) was used.

Figure imgf000097_0002
화합물 P-6 대신 화합물 P-8(22.9 g, 38.1 mmol ) , 브로모페난트렌 (2-bromophenanthrene) 대신 4ᅳ브로모 -1，1' :4'，] 터페닐 (4-bromo-l,l'：4',1' '-terphenyl )(11.8 g, 38.1 mmol)을 사용한 외에는 합성예 1-1과 동일한 방법으로 화합물 27(21.2 g, 수율 79 MS:[M+H]+= 704) 을 제조하였다.
Figure imgf000097_0002
Compound P-8 (22.9 g, 38.1 mmol) in place of Compound P-6, 4-bromo-1,1 ': 4',] terphenyl (4-bromo-l, in place of 2-bromophenanthrene) Compound 27 (21.2 g, yield 79 MS: [M + H] + = 704) in the same manner as in Synthesis Example 1-1, except that l ': 4', 1 '' -terphenyl) (11.8 g, 38.1 mmol) was used. Was prepared.

Figure imgf000098_0001
화합물 P-4(40.0 g, 162.3 mmol)과 2-([l,l'-biphenyl]-3-yl)-4- chloro-6-phenyl-l,3,5-triazine(55.8 g, 162.3 mmol)을 테트라하이드로퓨란 (500 ml)에 분산시킨 후, 2M 탄산칼륨수용액 (aq. K2C03)(67.2 ml, 486.9 讓 ol)을 첨가하고 테트라키스트리페닐포스피노팔라듐 [Pd(PPh3)4](3.8 g, 2 mol%)을 넣은 후 4시간 동안 교반 환류하였다. 상온으로 온도를 낮추고 생성된 고체를 여과하였다. 여과된 고체를 테트라하이드로퓨란과 에틸아세테이트로 재결정하고 여과한 뒤, 건조하여 화합물 P-9(69.5 g, 수율 84 ； MS:[M+H]+=510)를 제조하였다.
Figure imgf000098_0001
Compound P-4 (40.0 g, 162.3 mmol) and 2-([l, l'-biphenyl] -3-yl) -4-chloro-6-phenyl-l, 3,5-triazine (55.8 g, 162.3 mmol ) Is dispersed in tetrahydrofuran (500 ml), and then 2M aqueous potassium carbonate (aq.K 2 CO 3 ) (67.2 ml, 486.9 Pa) is added and tetrakistriphenylphosphinopalladium [Pd (PPh 3 ) 4 ] (3.8 g, 2 mol%) was added thereto, followed by stirring for 4 hours. The temperature was lowered to room temperature and the resulting solid was filtered. The filtered solid was recrystallized from tetrahydrofuran and ethyl acetate, filtered and dried to give compound P-9 (69.5 g, yield 84; MS: [M + H] + = 510).

Figure imgf000099_0001
P-9
Figure imgf000099_0001
P-9

화합물 P-9(70.5 g, 138.3 腿 ol) 비스 (피나콜라토)디보론 (Bis(pinacolato)diborone)(38.6 g, 152.13 mmol) 포타슘아세테이트 (potassium acetate)(40.7 g, 414.9 mmol), 테트라키스트리페닐포스피노팔라듐 (0) [Pd(PPh3)4](3.2 g, 2 mol«을 테트라하이드로퓨란 (600 ml) 에 넣고 12시간 동안 환류시켰다. 반웅이 종료된 후 상은으로 식힌 뒤 감압 증류하여 용매를 제거하였다. 이것을 클로로포름 (Chloroform)에 녹이고 물로 3회 씻어낸 뒤 유기층을 분리하여 황산 마그네슘 (Magnesium sulfate)으로 건조하였다. 이를 감압 증류하여 화합물 P-KK73.5 g, 수율 88 %； MS:[M+H]+=602)을 제조하였다. Compound P-9 (70.5 g, 138.3 腿 ol) bis (pinacolato) diborone (38.6 g, 152.13 mmol) potassium acetate (40.7 g, 414.9 mmol), tetrakis Triphenylphosphinopalladium (0) [Pd (PPh 3 ) 4 ] (3.2 g, 2 mol «was added to tetrahydrofuran (600 ml) and refluxed for 12 hours. The solvent was removed, which was dissolved in chloroform, washed three times with water, and the organic layer was separated and dried over magnesium sulfate, which was distilled under reduced pressure to obtain compound P-KK7 (3.5 g, yield 88%; MS). : [M + H] + = 602).

Figure imgf000099_0002
Figure imgf000099_0002

P-10  P-10

화합물 P-6 대신 화합물 P-KK22.9 g, 38.1 讓 ol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-브로모트리페닐렌 (2- bromotriphenylene)(11.7 g, 38.1 mmol)을 사용한 것 외에는 합성예 1—1과 동일한 방법으로 화합물 6(20.3 g, 수율 76 %; MS:[M+H]+= 702) 제조하였다. 2-bromotriphenylene (11.7 g, 38.1 mmol) was substituted for compound P-KK22.9 g, 38.1 讓 ol) and 2-bromophenanthrene instead of compound P-6. Synthesis Example 1-1 and Compound 6 (20.3 g, yield 76%; MS: [M + H] + = 702) was prepared in the same manner.

Figure imgf000100_0001
Figure imgf000100_0001

화합물 P-6 대신 화합물 P-10(22.9 g, 38.1 mmol), 2— 브로모페난트렌 ( 2-bromophenant hr ene ) 대신 4-브로모 -1，1' :4' ,1' '-터페닐- 2' '，3' '，4' ' ,5' '，6' '-디 5(4-bromo-l,l ：4' , 1 ' ' -terphenyl - 4-bromo-1,1 ': 4', 1'-terphenyl instead of compound P-10 (22.9 g, 38.1 mmol), 2—bromophenantrene instead of compound P-6 -2 '' ， 3 '' ， 4 '', 5 '' 6 '' -D 5 (4-bromo-l, l: 4 ', 1' '-terphenyl-

2' '，3' ' ,4' ' ,5' '，6' '― d5)(12.0 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 36(21.1 g, 수율 78 ', MS:[M+H]+= 709) 을 제조하였다. Compound 36 (21.1 g, yield 78) in the same manner as in Synthesis example 1-1, except that 2 '', 3 '', 4 '', 5 '', 6 '' -d5) (12.0 g, 38.1 mmol) was used. ' , MS: [M + H] + = 709).

Figure imgf000100_0002
브로모페난트렌 (2-bromophenanthrene) 대신 ( 1— [ 1， 1 '비페닐 ] -2-일)— 4- 브로모니프탈렌 (l-([l,l'-biphenyl]— 2-yl)-4-bromonaphthalene)(13.7 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 49(20.4 g, 수율 71 ； MS:[M+H]+= 754) 을 제조하였다.
Figure imgf000100_0002
Instead of 2-bromophenanthrene (1— [1, 1 'biphenyl] -2-yl) — 4-bromoniphthalene (l-([l, l'-biphenyl] — 2-yl) Compound 49 (20.4 g, yield 71; MS: [M + H] + = 754) was prepared in the same manner as in Synthesis Example 1-1 except that 4-bromonaphthalene) (13.7 g, 38.1 mmol) was used.

Figure imgf000101_0001
Figure imgf000101_0001

화합물 P-6 대신 화합물 P-10(22.9 g, 38.1 mmol), 브로모페난트렌 (2-bromophenanthrene) 대신 4-브로모 -1， 1 ' :4'， 1 ' 터페닐 (4-broir -l,l' :4' ,1' '-terpheny 1)(11.8 g, 38.1 mmol)을 사용한 외에는 합성예 1-1과 동일한 방법으로 화합물 61(19.8 g, 수율 74 MS:[M+H]+= 704) 을 제조하였다. 합성예 3-5: 화합물 70의 제조 Compound P-10 (22.9 g, 38.1 mmol) instead of compound P-6, 4-bromo-1, 1 ': 4', 1 'terphenyl (4-broir -l instead of 2-bromophenanthrene) , l ': 4', 1 '' -terpheny 1) (11.8 g, 38.1 mmol), except that Compound 61 (19.8 g, yield 74 MS: [M + H] + = was obtained in the same manner as in Synthesis Example 1-1. 704) was prepared. Synthesis Example 3-5: Preparation of Compound 70

Figure imgf000102_0001
Figure imgf000102_0001

화합물 P-6 대신 화합물 P-10(22.9 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 6'-브로모- Compound P-10 (22.9 g, 38.1 mmol) instead of compound P-6, 6'-bromo- instead of 2-bromophenanthrene

1,1'：3',1' '：4' ',Ι' ' '—쿼터페닐 (6'-bromo— 1,1'：3',1' '：4' '，1' ' '- quater phenyl )(14.7 g, 38.1 隱 ol)을 사용한 것 외에는 합성예 1—1과 동일한 방법으로 화합물 70(20.2 g, 수율 68 ； MS:[M+H]+= 780) 을 제조하였다. 1,1 '： 3', 1 '' ： 4 '', Ι '''—Quarterphenyl(6'-bromo—1,1' ： 3 ', 1''：4''，1'''- Compound 70 (20.2 g, yield 68; MS: [M + H] + = 780) was prepared in the same manner as in Synthesis Example 1-1, except that quater phenyl) (14.7 g, 38.1 dl ol) was used.

Figure imgf000102_0002
Figure imgf000102_0002

5-클로로 -2-메록시페닐보론산 ( (5-chloro-2-methoxypheny 1 )boroni c acid)(62.2 g, 333.5 隱 ol) 대신 (2-메특시페닐)보론산 ((2- methoxypheny 1 )boroni c acid)(50.7 g, 333.5 mmol)을 사용한 것 외에는 합성예 1과 동일한 방법으로 화합물 Q- 81.6 g, 수율 87 %;MS:[M+H]+=280)을 얻었다.

Figure imgf000103_0001
5-chloro-2-methoxyphenylboronic acid ((5-chloro-2-methoxypheny 1) boroni c acid) (62.2 g, 333.5 隱 ol) instead of (2-methoxyphenyl) boronic acid ((2-methoxypheny 1 ) Boroni c acid) (50.7 g, 333.5 mmol) was used in the same manner as in Synthesis example 1 to obtain compound Q-81.6 g, yield 87%; MS: [M + H] + = 280).
Figure imgf000103_0001

Q-1 Q-2  Q-1 Q-2

화합물 P-K85.0 g, 269.4 mmol) 대신 화합물 Q_l(75.7 g, 269.4 mmol) 을 사용한 것 외에는 합성예 1과 동일한 방법으로 화합물 Q-2(71.2 g, 수율 99 >;MS:[M+H]+=266)을 얻었다. Compound Q-2 (71.2 g, yield 99>; MS: [M + H) in the same manner as in Synthesis Example 1 except for using the compound Q_l (75.7 g, 269.4 mmol) instead of the compound P-K85.0 g, 269.4 mmol) ] + = 266).

Figure imgf000103_0002
Figure imgf000103_0002

Q-2 Q-3  Q-2 Q-3

화합물 P-2(80.0 g, 265.3 匪 ol) 대신 화합물 Q-2(70.9 g, 265.3 mmol) 을 사용한 것 외에는 합성예 1과 동일한 방법으로 화합물 Q— 3(62.3 g, 수율 95 %;MS:[M+H]+=246)을 얻었다. Compound Q-3 (62.3 g, Yield 95%; MS: [] in the same manner as in Synthesis Example 1, except that Compound Q-2 (70.9 g, 265.3 mmol) was used instead of Compound P-2 (80.0 g, 265.3 匪 ol). M + H] + = 246).

Figure imgf000103_0003
Figure imgf000103_0003

Q'3 Q-4 Q ' 3 Q-4

화합물 Q-3(40 g, 161.9 隱 ol)를 아세트산 (acetic acid) 200 ml에 용해시킨다. 여기에 요오드 (4.16 g, 81.0 匪 ol), 요오드산 (6.3 g, 36.0 mmol), 황산 (10 ml)을 넣고 65°C에서 3 h 동안 교반하였다. 반응이 종료된 후 상온으로 식히고， 물을 첨가한다. 생성된 고체를 필터하고 물로 세척한 뒤 를루엔과 에틸아세테이트로 재결정하여 화합물 Q-4(50.1 g, 수율 83 %； MS： [M+H] +=372 )을 얻었다. 합성예 4-1: 중간체 화합물 Q-5의 제조 Compound Q-3 (40 g, 161.9 μl) is dissolved in 200 ml of acetic acid. Iodine (4.16 g, 81.0 匪 ol), iodic acid (6.3 g, 36.0 mmol) and sulfuric acid (10 ml) were added thereto and stirred at 65 ° C for 3 h. After the reaction is completed, the mixture is cooled to room temperature and water is added. The resulting solid was filtered, washed with water and recrystallized with toluene and ethyl acetate to give compound Q-4 (50.1 g, yield 83%; MS: [M + H] + = 372). Synthesis Example 4-1 Preparation of Intermediate Compound Q-5

Figure imgf000104_0001
Figure imgf000104_0001

Q-5  Q-5

화합물 Q-4(30 g, 80.4 mmol), 4,4,5,5-tetramethyl-2-(triphenylen- 2-y 1 ) - 1 , 3 , 2-d i oxabor o 1 ane (28.5 g, 80.4 mmol) 를 테트라하이드로퓨란 (THF)300 ml에 녹였다. 여기에 탄산나트륨 (Na2C03) 2 M 용액 (120 mL), 테트라키스 (트리페닐포스핀)팔라듐 (0) [Pd(PPh3)4](1.9 g, 2 mol%)을 넣고 6 시간 환류시켰다. 반웅이 끝난 후 상온으로 냉각시키고， 생성된 흔합물을 물과 를루엔으로 3회 추출하였다. 를루엔층을 분리한 뒤 황산마그네슘 (magnesium sulfate)으로 건조하여 여과한 여액을 감압증류하여 얻은 흔합물을 클로로품， 에틸아세테이트를 이용해 재결정 하여 화합물 Q— 5(28.9 g, 수율 76 WIS: [M+H]+=473)을 얻었다. Compound Q-4 (30 g, 80.4 mmol), 4,4,5,5-tetramethyl-2- (triphenylen- 2-y 1)-1, 3, 2-di oxabor o 1 ane (28.5 g, 80.4 mmol ) Was dissolved in 300 ml of tetrahydrofuran (THF). Add sodium carbonate (Na 2 CO 3 ) 2 M solution (120 mL), tetrakis (triphenylphosphine) palladium (0) [Pd (PPh 3 ) 4 ] (1.9 g, 2 mol%), and reflux for 6 hours. I was. After the reaction was completed, the reaction mixture was cooled to room temperature, and the resultant mixture was extracted three times with water and toluene. The toluene layer was separated, dried over magnesium sulfate, and the filtrate was filtered and distilled under reduced pressure. The mixture was recrystallized with chloroform and ethyl acetate to give a compound Q-5 (28.9 g, yield 76 WIS: [M + H] + = 473).

Figure imgf000104_0002
Figure imgf000104_0002

Q-5  Q-5

Q-6  Q-6

화합물 Q-5(25 g, 52.8 隨 ol) 비스 (피나콜라토)디보론 (Bis(pinacolato)diborone)(14.9 g, 58.1 mmol) 포타슴아세테이트 (potassium acetate) (15.5 g, 158.4 mmol), 테트라키스트리페닐포스피노팔라듐 (0) [Pd(PPh3)4] (1.2 g, 2 mol%)을 테트라하이드로퓨란 (300 ml) 에 넣고 12시간 동안 환류시켰다. 반웅이 종료된 후 상온으로 식힌 뒤 감압 증류하여 용매를 제거하였다. 이것을 클로로포름 (Chloroform)에 녹이고 물로 3회 씻어낸 뒤 유기층을 분리하여 황산 마그네슘 (Magnesium sulfate)으로 건조하였다. 이를 감압 증류하여 화합물 Q-6C25.0 g, 수율 91 %； MS:[M+H]+=521)을 제조하였다. Compound Q-5 (25 g, 52.8 隨 ol) bis (pinacolato) diborone (14.9 g, 58.1 mmol) potassium acetate (15.5 g, 158.4 mmol), tetra Keystriphenylphosphinopalladium (0) [Pd (PPh 3 ) 4 ] (1.2 g, 2 mol%) was added to tetrahydrofuran (300 ml) and refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and then distilled under reduced pressure to remove the solvent. this It was dissolved in chloroform and washed three times with water, and then the organic layer was separated and dried over magnesium sulfate. This was distilled under reduced pressure to give compound Q-6C25.0 g, yield 91%; MS: [M + H] + = 521).

Figure imgf000105_0001
Figure imgf000105_0001

화합물 P-6 대신 2,4-diphenyl-6-(3-(4,4,5,5-tetramethyl-l,3,2- d i oxabor o 1 an-2-y 1 ) heny l)-l,3,5-triazine(16.6 g, 38.1 mmol ) , 2— 브로모페난트렌 (2-bromophenanthrene) 대신 화합물 Q-5(18.0 g, 38.1 mmol) 을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 7(19.0 g, 수율 71 ； MS:[M+H]+= 702) 을 제조하였다. Instead of compound P-6 2,4-diphenyl-6- (3- (4,4,5,5-tetramethyl-l, 3,2-di oxabor o 1 an-2-y 1) heny l) -l, Compound in the same manner as in Synthesis Example 1-1 except for using Compound Q-5 (18.0 g, 38.1 mmol) instead of 3,5-triazine (16.6 g, 38.1 mmol) and 2—bromophenanthrene 7 (19.0 g, yield 71; MS: [M + H] + = 702) was prepared.

Figure imgf000105_0002
Figure imgf000105_0002

화합물 P-6 대신 화합물 Q-6(19.8 g, 38.  Compound Q-6 instead of compound P-6 (19.8 g, 38.

브로모페난트렌 (2-bromophenanthrene) 대신 Instead of 2-bromophenanthrene

( d i benzo [b,d] fur an— 4— y 1 )一 6— pheny 1 - 1 , 3 , 5-t r i az i ne ( 13.6 g 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 8(19.9 g, 수을 73 %； MS:[M+H]+= 716) 을 제조하였다. (di benzo [b, d] fur an— 4— y 1) 一 6— pheny 1-1, 3, 5-tri az i ne (13.6 g A compound 8 (19.9 g, 73% water; MS: [M + H] + = 716) was prepared in the same manner as in Synthesis Example 1-1 except for use.

Figure imgf000106_0001
Figure imgf000106_0001

화합물 P-6 대신 화합물 Q-6 19.8 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-chloro-4- 19.8 g, 38.1 mmol) instead of compound P-6, 2-chloro-4- instead of 2-bromophenanthrene

( d i benzo [ b , d] t h i ophen-3-y 1 ) -6-pheny 1 - 1 , 3 , 5-t r i az i ne ( 14.2 g, 38.1 匪 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 19(19.5 g, 수율 70 %； MS:[M+H]+= 732) 을 제조하였다. Synthesis Example 1-1 and except that (di benzo [b, d] thi ophen-3-y 1) -6-pheny 1-1, 3, 5-tri az i ne (14.2 g, 38.1 匪 ol) Compound 19 (19.5 g, yield 70%; MS: [M + H] + = 732) was prepared in the same manner.

Figure imgf000106_0002
Figure imgf000106_0002

Q-6 화합물 48 화합물 P-6 대신 화합물 Q-6 19.8 g, 38.1 瞧 ol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 4- (4_ch lor으 6— phenyl— 1， 3,5— t r i az i η-2-y 1 ) -9-pheny 1 -9H-car bazo 1 e ( 16.5 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 48(22.3 g, 수율 74 ； MS:[M+H]+= 791) 을 제조하였다.

Figure imgf000107_0001
Q-6 Compound 48 Instead of compound P-6 Compound 1-6 g, 38.1 瞧 ol), 2- (bromophenanthrene) 4- (4_chlor 6-phenyl— 1, 3,5— Tri az i η-2-y 1) -9-pheny 1 -9H-car bazo 1 e (16.5 g, 38.1 mmol) was obtained in the same manner as in Synthesis Example 1-1 except that Compound 48 (22.3 g, yield 74) was obtained. MS: [M + H] + = 791).
Figure imgf000107_0001

화합울 58 화합물 P-6 대신 화합물 Q-6(19.8 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-(2-bromophenyl )-4- Compound 58 Instead of compound P-6, compound Q-6 (19.8 g, 38.1 mmol), 2- (2-bromophenyl) -4- instead of 2-bromophenanthrene

(dibenzo[b，d]furan— 4— yl)— 6— phenyl— 1,3,5— tr.iazi g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 58(18.7 g, 수율 62 %; MS:[M+H]+= 792) 을 제조하였다. Compound 58 (18.7 g) in the same manner as in Synthesis Example 1-1 except for using (dibenzo [b ， d] furan— 4—yl) — 6—phenyl— 1,3,5—tr.iazi g, 38.1 mmol). , Yield 62%; MS: [M + H] + = 792).

Figure imgf000107_0002
Figure imgf000107_0002

4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-l,3,2- dioxaborolane(28.5 g, 80.4 mmol) 대신 4,4,5,5_tetramethyl-2- ( henant hr en-2-y l)-l,3,2-dioxaborolane(24.5 g, 80.4 mmol) 를 사용한 것 외에는 합성예 4-1과 동일한 방법으로 화합물 Q-7(20.0 g, 수율 59 %； MS:[M+H]+= 423) 을 제조하였다.

Figure imgf000108_0001
4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -l, 3,2-dioxaborolane (28.5 g, 80.4 mmol) instead of 4,4,5,5_tetramethyl-2- (henant hr en- Compound Q-7 (20.0 g, yield 59%; MS: [M + H] in the same manner as in Synthesis Example 4-1 except for using 2-yl) -l, 3,2-dioxaborolane (24.5 g, 80.4 mmol) ] + = 423).
Figure imgf000108_0001

Q-7 화합물 Q_5(25 g, 52.8匪 ol) 대신 화합물 Q_7(22.4 g, 52.8隱 ol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 Q-8(21.6 g, 수율 87 %； MS:[M+H]+= 471) 을 제조하였다. Q-7 Compound Q-8 (21.6 g, Yield 87%; MS in the same manner as in Synthesis Example 4-2) except that compound Q_7 (22.4 g, 52.8 隱 ol) was used instead of compound Q_5 (25 g, 52.8 匪 ol). : [M + H] + = 471).

Figure imgf000108_0002
Figure imgf000108_0002

화합물 P-6 대신 화합물 Q-8U7.9 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2— (4-chlorophenyl )-4- ( d i benzo [ b , d ] f ur an-4-y 1 ) -6-pheny l-l,3,5-triazine(16.5 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 10(18.4 g, 수율 65 %； MS:[M+H]+= 742) 을 제조하였다. 합성예 5-4: 화합물 15의 제조 Compound Q-8U7.9 g, 38.1 mmol) instead of compound P-6, 2-bromophenanthrene instead of 2— (4-chlorophenyl) -4- (di benzo [b, d] f ur an Compound 10 (18.4 g, yield 65%; MS: [) in the same manner as in Synthesis Example 1-1 except for using 4-y 1) -6-pheny ll, 3,5-triazine (16.5 g, 38.1 mmol). M + H] + = 742). Synthesis Example 5-4 Preparation of Compound 15

Figure imgf000109_0001
Figure imgf000109_0001

Q-8 화합을 15  Q-8 Unity 15

화합물 P-6 대신 화합물 Q-8 17.9 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-chloro-4-(4-(9,9-dimethyl- 9H- f 1 uor en- 1-y 1 ) heny 1 ) -6-pheny l-l,3,5-triazine(17.5 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 15(15.8 g, 수율 54 %； MS: [M+H]+= 768) 을 제조하였다.  17.9 g, 38.1 mmol) instead of compound P-6, 2-chloro-4- (4- (9,9-dimethyl-9H-f 1 uor en) instead of 2-bromophenanthrene Compound 15 (15.8 g, yield 54%) in the same manner as in Synthesis example 1-1 except for using 1-y 1) heny 1) -6-pheny ll, 3,5-triazine (17.5 g, 38.1 mmol); MS: [M + H] < + > = 768).

Figure imgf000109_0002
Figure imgf000109_0002

Q-9  Q-9

4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-l,3,2- d i oxabor 0 lane (28.5 g, 80.4 mmol) 대신 4,4,5,5-tetramethyl-2- ( henant hr en-9-y 1 ) - 1 , 3 , 2-d i oxabor o 1 ane (24.5 g, 80.4 mmol ) 를 사용한 것 외에는 합성예 4-1과 동일한 방법으로 화합물 Q-9(20.8 g, 수율 61 %; MS:[M+H]+= 423) 을 제조하였다. 합성예 6-2: 중간체 화합물 Q-10의 제조

Figure imgf000110_0001
4,4,5,5-tetramethyl-2- (triphenylen- 2-yl) -l, 3,2- di oxabor 0 lane (28.5 g, 80.4 mmol) instead of 4,4, 5, 5-tetramethyl- 2 - (hent hr en-9-y 1)-1, 3, 2-di oxabor o 1 ane (24.5 g, 80.4 mmol) except that the compound Q-9 (20.8 g, Yield 61%; MS: [M + H] + = 423). Synthesis Example 6-2: Preparation of Intermediate Compound Q-10
Figure imgf000110_0001

Q-9 d-10  Q-9 d-10

화합물 Q_5(25 g, 52.8 mmol) 대신 화합물 Q-7(22.4 g, 52.8 mmol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 Q-10(21.1 g, 수율 85 %； MS:[M+H]+= 471) 을 제조하였다. Compound Q-10 (21.1 g, yield 85%; MS: [M] in the same manner as in Synthesis Example 4-2 except for using compound Q-7 (22.4 g, 52.8 mmol) instead of compound Q_5 (25 g, 52.8 mmol). + H] + = 471).

Figure imgf000110_0002
Figure imgf000110_0002

화합물 P— 6 대신 화합물 Q-8 17.9 g, 38.1 mmol), 2- 브로모페난트렌 (2-broiTOphenanthrene) 대신 2-(3-chlorophenyl )— 4- ( d i benzo [ b , d ] f ur an-3-y 1 ) -6-pheny l-l,3,5-triazine(16.6 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 50(14.4 g, 수율 51 ； MS:[M+H]+= 742) 을 제조하였다. Compound Q-8 instead of compound Q-8 17.9 g, 38.1 mmol), 2- (3-chlorophenyl) instead of 2-broiTOphenanthrene— 4- (di benzo [b, d] f ur an- Compound 50 (14.4 g, yield 51; MS: [M +] in the same manner as in Synthesis Example 1-1 except for using 3-y 1) -6-pheny ll, 3,5-triazine (16.6 g, 38.1 mmol). H] + = 742).

Figure imgf000110_0003
4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-l,3,2- di oxaboro lane (28.5 g, 80.4 mmol) 대신 2— (chrysen-S-y -HS.S- tetramethyl-l ^-dioxaborolane S g, 80.4 mraol) 를 사용한 것 외에는 합성예 4-1과 동일한 방법으로 화합물 Q-1K23.6 g, 수율 62 %； MS:[M+H]+= 473) 을 제조하였다.
Figure imgf000110_0003
4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -l, 3,2-di oxaboro lane (28.5 g, 80.4 mmol) instead of 2— (chrysen-Sy -HS.S- tetramethyl- Compound Q-1K23.6 g, yield 62%; MS: [M + H] + = 473) was prepared in the same manner as in Synthesis Example 4-1, except that l ^ -dioxaborolane S g, 80.4 mraol) was used.

Figure imgf000111_0001
Figure imgf000111_0001

Q-11 Q -12  Q-11 Q -12

화합물 Q-5(25.0 g, 52.8 匪 ol) 대신 화합물 Q-ll(25.0 g, 52.8 mmol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 Q-12(22.5 g, 수율 82 %; MS:[M+H]+= 521) 을 제조하였다. Compound Q-12 (22.5 g, Yield 82%; MS) in the same manner as in Synthesis Example 4-2 except for using the compound Q-ll (25.0 g, 52.8 mmol) instead of the compound Q-5 (25.0 g, 52.8 匪 ol) : [M + H] + = 521).

Figure imgf000111_0002
Figure imgf000111_0002

화합물 14  Compound 14

화합물 P-6 대신 화합물 Q— 12(17.9 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-(2-chlorophenyl )-4- (dibenzo [b , d] f uran-l-y 1 )-6-phenyl-l , 3 , 5-t r i azine( 16.5 g, 38.1 瞧 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 14(14.5 g, 수율 48 %； MS:[M+H]+= 792) 을 제조하였다. Compound Q— 12 (17.9 g, 38.1 mmol) instead of compound P-6, 2- (2-chlorophenyl) -4- (dibenzo [b, d] f uran-ly instead of 2-bromophenanthrene) 1) Compound 14 (14.5 g, yield) in the same manner as in Synthesis Example 1-1 except for using 6-phenyl-l, 3, 5-triazine (16.5 g, 38.1 瞧 ol) 48%; MS: [M + H] + = 792).

Figure imgf000112_0001
Figure imgf000112_0001

Q-13  Q-13

4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-l,3,2- dioxaborolane(28.5 g, 80.4 隱 ol) 대신 4,4,5,5-tetramethyl-2-(4- ( henant hr en-9-y 1 ) heny 1 ) - 1 , 3 , 2-d i oxabor o 1 ane (30.6 g, 80.4 mmol ) 를 사용한 것 외에는 합성예 4-1과 동일한 방법으로 화합물 Q-13(29.3 g, 수율 73 ； MS:[M+H]+= 499) 을 제조하였다. 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -l, 3,2-dioxaborolane (28.5 g, 80.4 隱 ol) instead of 4,4,5,5-tetramethyl-2- (4 -Compound Q-13 in the same manner as in Synthesis Example 4-1, except that (henant hr en-9-y 1) heny 1)-1, 3, 2-dioxabor o 1 ane (30.6 g, 80.4 mmol) was used. (29.3 g, yield 73; MS: [M + H] + = 499) was prepared.

Figure imgf000112_0002
Figure imgf000112_0002

화합물 Q-5(25.0 g, 52.8 匪 ol) 대신 화합물 Q-13(26.4 g, 52.8 隱 ol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 Q-14(24.5 g, 수율 85 %； MS:[M+H]+= 547) 을 제조하였다. 합성예 8-3: 화합물 17의 제조 Compound Q-14 (24.5 g, yield 85%) in the same manner as in Synthesis example 4-2 except for using compound Q-13 (26.4 g, 52.8 2.8 ol) instead of compound Q-5 (25.0 g, 52.8 匪 ol); MS: [M + H] + = 547) was prepared. Synthesis Example 8-3 Preparation of Compound 17

Figure imgf000113_0001
Figure imgf000113_0001

Q-14  Q-14

화합울 17  Harmony Wool 17

화합물 P-6 대신 화합물 Q-14(20.8 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-([l,l'-biphenyl]-2-yl)-4- chloro-6-phenyl-l,3,5-triazine(13.1 g, 38.1 隱 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 17(18.9 g, 수율 68 ； MS:[M+H]+= 728) 을 제조하였다. Compound Q-14 (20.8 g, 38.1 mmol) instead of compound P-6, 2-([l, l'-biphenyl] -2-yl) -4-chloro- instead of 2-bromophenanthrene Compound 17 (18.9 g, yield 68; MS: [M + H] + = in the same manner as in Synthesis Example 1-1, except that 6-phenyl-l, 3,5-triazine (13.1 g, 38.1 μl ol) was used 728).

Figure imgf000113_0002
Figure imgf000113_0002

Q-15  Q-15

4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-l,3,2- dioxaborolane(28.5 g, 80.4 隱 ol) 대신 2-( [1， 1 ' -biphenyl ]— 4-yl )- 4,4,5,5-tetramethyl-l,3,2-dioxaborolane(22.5 g, 80.4 mmol) 를 사용한 것 외에는 합성예 4-1과 동일한 방법으로 화합물 Q-15(25.7 g, 수율 80 ¾; MS:[M+H]+= 399) 을 제조하였다. 합성예 9-2: 중간체 화합물 Q-16의 제조 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -l, 3,2-dioxaborolane (28.5 g, 80.4 隱 ol) instead of 2- ([1, 1 '-biphenyl] — 4- Compound Q-15 (25.7 g, Yield 80) in the same manner as in Synthesis Example 4-1, except that yl) -4,4,5,5-tetramethyl-l, 3,2-dioxaborolane (22.5 g, 80.4 mmol) was used. ¾; MS: [M + H] + = 399). Synthesis Example 9-2: Preparation of Intermediate Compound Q-16

Figure imgf000114_0001
Figure imgf000114_0001

Q-15 Q-16  Q-15 Q-16

화합물 Q-5(25.0 g, 52.8 醒 ol) 대신 화합물 Q-13(21.1 g, 52.8 瞧 ol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 Q-16(20.3 g, 수율 86 %； MS:[M+H]+= 447) 을 제조하였다. Compound Q-16 (20.3 g, yield 86%) in the same manner as in Synthesis example 4-2 except for using compound Q-13 (21.1 g, 52.8 瞧 ol) instead of compound Q-5 (25.0 g, 52.8 醒 ol); MS: [M + H] + = 447).

Figure imgf000114_0002
Figure imgf000114_0002

화합울 30  Harmony Wool 30

화합물 P-6 대신 화합물 Q-16U7.0 g, 38.1 mmol), 2- 브로모페난트렌 (2— bromophenanthrene) 대신 2-chloro_4-(3— Compound Q-16U7.0 g, 38.1 mmol) instead of compound P-6, 2-chloro_4- (3—instead of 2-bromophenanthrene)

(dibenzo [b,d] furan-l-yl ) henyl ) -6-pheny 1-1 ,3,5-triazine(16.5 g, 38.1 瞧 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 30(18.9 g 수율 69 ； MS:[M+H]+= 718) 을 제조하였다. 합성예 9-4: 화합물 39의 제조 (Dibenzo [b, d] furan-l-yl) henyl) -6-pheny 1-1,3,5-triazine (16.5 g, 38.1 瞧 ol), except that compound was prepared in the same manner as in Synthesis Example 1-1 30 (18.9 g yield 69; MS: [M + H] + = 718) was prepared. Synthesis Example 9-4: Preparation of Compound 39

Figure imgf000115_0001
Figure imgf000115_0001

화합물 P-6 대신 화합물 Q-16 17.0 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenantlirene) 대신 2-([1，1' :3'，1' '-terphenyl]- 5 ' -y 1 ) -4-ch 1 or ο-6-pheny 1 - 1 , 3 , 5-t r i az i ne ( 16.0 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 39(17.4 g, 수율 65 ； MS:[M+H]+= 704) 을 제조하였다. Instead of compound P-6, compound Q-16 17.0 g, 38.1 mmol), 2-bromophenantrene (2-bromophenantlirene) instead of 2-([1,1 ': 3' ， 1 '' -terphenyl] -5 '- y 1) Compound 39 (17.4) in the same manner as in Synthesis Example 1-1, except that 4-ch 1 or ο-6-pheny 1-1, 3, 5-tri az i ne (16.0 g, 38.1 mmol) was used g, yield 65; MS: [M + H] + = 704).

Figure imgf000115_0002
Figure imgf000115_0002

화합물 P-6 대신 화합물 Q-16 17.0 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-(3-chlorophenyl ^ ^-(g^- cl i me t hy 1 -9H- f 1 uoren-3-y 1 ) heny 1 ) -6-pheny l-l,3,5-triazine(20.4 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 44(19.4 g 수율 62 %； MS:[M+H]+= 820) 을 제조하였다.

Figure imgf000116_0001
Instead of compound P-6, compound Q-16 17.0 g, 38.1 mmol), 2-bromophenanthrene instead of 2- (3-chlorophenyl ^ ^-(g ^-cl i me t hy 1 -9H- f 1 uoren-3-y 1) heny 1) -6-pheny ll, 3,5-triazine (20.4 g, 38.1 mmol) was used in the same manner as in Synthesis Example 1-1 except that Compound 44 (19.4 g yield 62 %; MS: [M + H] + = 820).
Figure imgf000116_0001

화 울 63  Tuesday Wool 63

화합물 P-6 대신 화합물 Q— 16(17.0 g, 38.1 mmol), 2- 브로모페난트렌 (2— bromophenanthrene) 대신 2— ([1，1' :3'，1' '-terphenyl]-4— y 1 ) -4-ch 1 or ο-6-pheny 1 - 1 , 3 , 5- 1 r i az i ne ( 16.0 g, 38.1 隱 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 63(17.4 g, 수율 65 %； MS:[M+H]+= 704) 을 제조하였다. Compound Q— 16 (17.0 g, 38.1 mmol) instead of compound P-6, 2— ([1，1 ': 3' ， 1 '' -terphenyl] -4— instead of 2-bromophenanthrene y 1) Compound 63 was used in the same manner as in Synthesis Example 1-1 except that 4-ch 1 or ο-6-pheny 1-1, 3, 5- 1 ri az i ne (16.0 g, 38.1 隱 ol) was used. (17.4 g, yield 65%; MS: [M + H] + = 704) was prepared.

Figure imgf000116_0002
Figure imgf000116_0002

화합물 P-6 대신 화합물 Q-16(17.0 g, 38.1 隱 ol), 2- 브로모페난트렌 (2— bromophenanthrene) 대신 2-chloro_4-(3- Instead of compound P-6, compound Q-16 (17.0 g, 38.1 隱 ol), 2-bromophenanthrene (2-—bromophenanthrene) 2-chloro_4- (3-

( d i benzo [ b , d ] f ur an-4-y 1 ) heny 1 ) -6-pheny 1-1,3,5-triazine (16.5 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 64(17.5 g, 수율 64 %； MS:[M+H]+= 718) 을 제조하였다. 합성예 9-8: 화합물 74의 제조 (Di benzo [b, d] f ur an-4-y 1) heny 1) -6-pheny 1-1,3,5-triazine (16.5 g, 38.1 mmol) except for using Synthesis Example 1-1 Compound 64 (17.5 g, yield 64%; MS: [M + H] + = 718) was prepared in the same manner. Synthesis Example 9-8: Preparation of Compound 74

화합물 P-6 대신 화합물 Q-16(17.0 g, 38.1 醒 ol), 2— 브로모페난트렌 (2-bromophenan1;hrene) 대신 2-(4-chlon)phenyl)-4— ( d i benzo [ b , d ] t h i ophen-2-y 1 ) -6-pheny 1-1,3,5-triazine (17.1 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 74(17.3 g, 수율.62 %； MS:[M+H]+= 734) 을 제조하였다. Compound Q-16 (17.0 g, 38.1 醒 ol) instead of P-6, 2—2- (4-chlon) phenyl) -4— (di benzo [b, instead of 2-bromophenan1; hrene) d] compound 74 (17.3 g, yield) in the same manner as in Synthesis Example 1-1 except that thi ophen-2-y 1) -6-pheny 1-1,3,5-triazine (17.1 g, 38.1 mmol) was used .62%; MS: [M + H] + = 734) was prepared.

Figure imgf000117_0002
Figure imgf000117_0002

Q-17  Q-17

4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-l,3,2- dioxaborolane(28.5 g, 80.4 瞧 ol) 대신 6'— chloro— 1,1' :3'，1' ' :4' '，1' ' '一 quater henyl (27.4 g, 80.4 mmol) 를 사용한 것 외에는 합성예 4-1과 동일한 방법으로 화합물 Q-17(28.0 g, 수율 63 ； MS:[M+H]+= 551) 을 제조하였다. 합성예 10-2: 중간체 화합물 Q-18의 제조 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -l, 3,2-dioxaborolane (28.5 g, 80.4 瞧 ol) 6'— chloro— 1,1 ': 3' ， 1 Compound Q-17 (28.0 g, Yield 63; MS: [M +] in the same manner as in Synthesis Example 4-1, except that '': 4 '', 1 '''quater henyl (27.4 g, 80.4 mmol) was used. H] + = 551). Synthesis Example 10-2 Preparation of Intermediate Compound Q-18

Figure imgf000118_0001
Figure imgf000118_0001

CM 7 Q-18 화합물 Q_5(25.0 g, 52.8 mmol) 대신 화합물 Q-17(29.1 g, 52.8 隱 ol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 Q-18(25.9 g, 수율 82 %； MS:[M+H]+= 599) 을 제조하였다. CM 7 Q-18 Compound Q-18 (25.9 g, Yield 82) in the same manner as in Synthesis Example 4-2 except that Compound Q-17 (29.1 g, 52.8 mmol) was used instead of Compound Q_5 (25.0 g, 52.8 mmol). %; MS: [M + H] + = 599) was prepared.

Figure imgf000118_0002
Figure imgf000118_0002

화합물 P-6 대신 화합물 Q-18(22.8 g, 38.1 隱 ol), 2- 브로모페난트렌 (2— bromophenanthrene) 대신 4-chloro— 2,6- diphenylpyrimidine(10.2 g, 38.1 誦 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 31(18.2 g, 수율 68 %； MS:[M+H]+= 703) 을 제조하였다. 합성예 11-1: 중간체 화합물 Q-19의 제조 Use of 4-chloro- 2,6-diphenylpyrimidine (10.2 g, 38.1 誦 ol) instead of compound Q-18 (22.8 g, 38.1 隱 ol) and 2-bromophenanthrene instead of compound P-6 A compound 31 (18.2 g, yield 68%; MS: [M + H] + = 703) was prepared in the same manner as in Synthesis example 1-1. Synthesis Example 11-1 Preparation of Intermediate Compound Q-19

Figure imgf000119_0001
Figure imgf000119_0001

Q-19 Q-19

4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-l,3,2- dioxaborolane(28.5 g, 80.4 mmol) 대신 2-( [1， 1' :2'， 1' '— terphenyl]-2- yl)-4,4,5,5-tetramethyl-l,3,2-dioxaborolane(28.6 g, 80.4 mmol) 를 사용한 것 외에는 합성예 4-1과 동일한 방법으로 화합물 Q-19(25.2 g, 수율 66 %; MS:[M+H]+= 475) 을 제조하였다. 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -l, 3,2-dioxaborolane (28.5 g, 80.4 mmol) instead of 2- ([1, 1 ': 2', 1 '' — Compound Q-19 in the same manner as in Synthesis Example 4-1, except that terphenyl] -2-yl) -4,4,5,5-tetramethyl-l, 3,2-dioxaborolane (28.6 g, 80.4 mmol) was used. (25.2 g, yield 66%; MS: [M + H] + = 475) was prepared.

Figure imgf000119_0002
Figure imgf000119_0002

Q-20  Q-20

Q-19  Q-19

화합물 Q-5(25.0 g, 52.8 mmol) 대신 화합물 Q-19(25.1 g, 52.8 醒 ol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 Q-20(22.1 g, 수율 80 %； MS:[M+H]+= 523) 을쩨조하였다. 합성예 11-3: 화합물 32의 제조 Compound Q-20 (22.1 g, yield 80%; MS) in the same manner as in Synthesis Example 4-2 except for using compound Q-19 (25.1 g, 52.8 mmol) in place of compound Q-5 (25.0 g, 52.8 mmol). : [M + H] + = 523). Synthesis Example 11-3: Preparation of Compound 32

Figure imgf000120_0001
Figure imgf000120_0001

51합울 32 51 Wool 32

화합물 p-6 대신 화합물 Q-20C19.9 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-chloro-4-(naphthalen-l— yl )- 6-pheny 1 -1 , 3 , 5-t r i az i ne ( 12.1 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 32(15.8 g, 수율 61 ； MS:[M+H]+= 678) 을 제조하였다. Compound Q-20C19.9 g, 38.1 mmol) instead of p-6, 2-chloro-4- (naphthalen-l— yl) -6-pheny 1 -1, instead of 2-bromophenanthrene Compound 32 (15.8 g, yield 61; MS: [M + H] + = 678) was prepared in the same manner as in Synthesis Example 1-1 except for using 3, 5-tri az i ne (12.1 g, 38.1 mmol). It was.

Figure imgf000120_0002
Figure imgf000120_0002

4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-l,3,2- dioxaborolane(28.5 g, 80.4 mmol) 대신 [1，1' :4'，1' '-terphenyl]_3- ylboronic acid(22.0 g, 80.4 醒 ol) 를 사용한 것 외에는 합성예 4-1과 동일한 방법으로 화합물 Q-2K27.1 g, 수율 71 ； MS:[M+H]+= 475) 을 제조하였다. 합성예 12-2:중간체 화합물 Q-22의 제조 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -l, 3,2-dioxaborolane (28.5 g, 80.4 mmol) instead of [1,1 ': 4' ， 1 '' -terphenyl] Compound Q-2K27.1 g, yield 71; MS: [M + H] + = 475) were prepared in the same manner as in Synthesis Example 4-1 except that _3-ylboronic acid (22.0 g, 80.4 醒 ol) was used. . Synthesis Example 12-2 Preparation of Intermediate Compound Q-22

Figure imgf000121_0001
Figure imgf000121_0001

화합물 Q_5(25.0 g, 52.8 mmol) 대신 화합물 Q-21(25.1 g, 52.8 誦 ol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 Q-22(21.5 g, 수율 78 %； MS:[M+H]+= 523) 을 제조하였다. Compound Q-22 (21.5 g, Yield 78%; MS: [] in the same manner as in Synthesis Example 4-2 except that Compound Q-21 (25.1 g, 52.8 mmol) was used instead of Compound Q_5 (25.0 g, 52.8 mmol). M + H] + = 523).

Figure imgf000121_0002
Figure imgf000121_0002

화 if울 33  Gorgeous if wool 33

화합물 P— 6 대신 화합물 Q-22U9.9 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-chloro— 4- Compound Q-22U9.9 g, 38.1 mmol) instead of compound P-6, 2-chloro- 4- instead of 2-bromophenanthrene

(dibenzo[b , d] furan-l-yl )-6-pheny 1-1 , 3 , 5~tr i azine( 13.6 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 33(18.8 g, 수율 69 ； MS:[M+H]+= 718) 을 제조하였다. 합성예 12-4: 화합물 67의 제조 Compound 33 in the same manner as in Synthesis Example 1-1, except that (dibenzo [b, d] furan-l-yl) -6-pheny 1-1, 3, 5 to tr iazine (13.6 g, 38.1 mmol) was used. (18.8 g, yield 69; MS: [M + H] + = 718) was prepared. Synthesis Example 12-4: Preparation of Compound 67

Figure imgf000122_0001
Figure imgf000122_0001

화 ϋ튤 67  Japanese Tulle 67

화합물 Ρ-6 대신 화합물 Q-22(19.9 g, 38.1 匪 ol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2_chloro-4_ Compound Q-22 (19.9 g, 38.1 匪 ol) instead of compound Ρ-6, 2-chloro-4 instead of 2-bromophenanthrene

(dibenzo[b,d]fur an-2-y 1 ) -6-pheny l-l,3,5-triazine(13.6 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 67(17.2 g, 수율 63 %； MS:[M+H]+= 718) 을 제조하였다. Compound 67 (17.2) in the same manner as in Synthesis Example 1-1 except for using (dibenzo [b, d] fur an-2-y 1) -6-pheny ll, 3,5-triazine (13.6 g, 38.1 mmol). g, yield 63%; MS: [M + H] + = 718).

Figure imgf000122_0002
Figure imgf000122_0002

4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-l,3,2- dioxaborolane(28.5 g, 80.4 mmol) 대신 [1，1' :3'，1' '-terphenyl]-3_ ylboronic acid(22.0 g, 80.4 匪 ol) 를 사용한 것 외에는 합성예 4-1과 동일한 방법으로 화합물 Q-23(24.5 g, 수율 64 %； MS:[M+H]+= 475) 을 제조하였다. 합성예 13-2: 중간체 화합물 Q-24의 제조 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -l, 3,2-dioxaborolane (28.5 g, 80.4 mmol) instead of [1,1 ': 3' ， 1 '' -terphenyl] Compound Q-23 (24.5 g, Yield 64%; MS: [M + H] + = 475) was prepared in the same manner as in Synthesis Example 4-1 except for using -3_ylboronic acid (22.0 g, 80.4 匪 ol) It was. Synthesis Example 13-2: Preparation of Intermediate Compound Q-24

Figure imgf000123_0001
Figure imgf000123_0001

화합물 Q-5(25.0 g, 52.8 mmol) 대신 화합물 Q-23(25.1 g, 52.8 mmol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 Q— 24(20.7 g, 수율 75 %; MS:[M+H]+= 523) 을 제조하였다. Compound Q— 24 (20.7 g, Yield 75%; MS: Compounds Q-23 (25.1 g, 52.8 mmol) instead of Compound Q-5 (25.0 g, 52.8 mmol) in the same manner as in Synthesis Example 4-2 [M + H] + = 523).

Figure imgf000123_0002
Figure imgf000123_0002

화합물 P-6 대신 화합물 Q-24 19.9 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenan1;hrene) 대신 2-(4-chlorophenyl ^S- diphenyl-U^-tr iazine(13.1 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 34(19.6 g, 수율 73 %; MS:[M+H]+= 704) 을 제조하였다. 합성예 13-4: 화합물 69의 제조 Compound Q-24 19.9 g, 38.1 mmol) instead of compound P-6, 2- (4-chlorophenyl ^ S-diphenyl-U ^ -tr iazine (13.1 g, instead of 2-bromophenan1; hrene) Compound 34 (19.6 g, yield 73%; MS: [M + H] + = 704) was prepared in the same manner as in Synthesis Example 1-1 except for using 38.1 mmol). Produce

Figure imgf000124_0001
Figure imgf000124_0001

화합물 69  Compound 69

화합물 P-6 대신 화합물 Q-24(19.9 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-(3— chlorophenyl ^ ^- diphenyl-U^-triazine lS.1 g, 38.1 睡 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 69(18.8 g, 수율 70 ； MS:[M+H]+= 704) 을 제조하였다. Compound Q-24 (19.9 g, 38.1 mmol) instead of compound P-6, 2- (3—chlorophenyl ^ ^-diphenyl-U ^ -triazine lS.1 g, 38.1 instead of 2-bromophenanthrene Compound 69 (18.8 g, yield 70; MS: [M + H] + = 704) was prepared in the same manner as in Synthesis Example 1-1 except for using ol).

Figure imgf000124_0002
Figure imgf000124_0002

4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-l,3,2- d i oxabor o 1 ane (28.5 g, 80.4 mmol ) 대신 [ 1 , 1 ' -b i pheny 1 ] -3-y 1 bor on i c acid(15.9 g, 80.4 mmol) 를 사용한 것 외에는 합성예 4-1과 동일한 방법으로 화합물 Q-25(21.8 g, 수율 68 %; MS:[M+H]+= 399) 을 제조하였다. 합성예 14-2: 중간체 화합물 Q-26의 제조 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -l, 3,2-di oxabor o 1 ane (28.5 g, 80.4 mmol) instead of [1, 1 '-bi pheny 1]- Compound Q-25 (21.8 g, yield 68%; MS: [M + H] + = 399 in the same manner as in Synthesis Example 4-1 except for using 3-y 1 bor on ic acid (15.9 g, 80.4 mmol) ) Was prepared. Synthesis Example 14-2: Preparation of Intermediate Compound Q-26

Figure imgf000125_0001
화합물 Q_5(25.0 g, 52.8 mmol) 대신 화합물 Q-25(21.1 g, 52.8 mmol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 Q_26(16.5 g, 수율 70 ； MS:[M+H]+= 447) 을 제조하였다.
Figure imgf000125_0001
Compound Q_26 (16.5 g, yield 70; MS: [M + H]) in the same manner as in Synthesis Example 4-2 except that compound Q-25 (21.1 g, 52.8 mmol) was used instead of compound Q_5 (25.0 g, 52.8 mmol). + = 447) was prepared.

Figure imgf000125_0002
Figure imgf000125_0002

화합울 35  Harmony Wool 35

화합물 P-6 대신 화합물 Q-26(19.9 g, 38.1 瞧 ol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-( [1, 1 ' :2 '， Γ '— terphenyl ]-3- y 1 ) -4-ch 1 or ο-6-pheny 1 - 1 , 3 , 5-t r i az i ne ( 16.0 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 35(17.4 g, 수율 65 %; MS:[M+H]+= 704) 을 제조하였다. 합성예 14-4: 화합물기의 제조 Compound Q-26 instead of compound P-6 (19.9 g, 38.1 瞧 ol), 2-bromophenanthrene instead of 2- ([1, 1 ': 2', Γ '— terphenyl] -3- y 1) Compound 35 (17.4) in the same manner as in Synthesis Example 1-1, except that 4-ch 1 or ο-6-pheny 1-1, 3, 5-tri az i ne (16.0 g, 38.1 mmol) was used g, yield 65%; MS: [M + H] + = 704). Synthesis Example 14-4: Preparation of Compound Group

Figure imgf000126_0001
Figure imgf000126_0001

화합물 P-6 대신 화합물 Q-26(19.9 g, 38.1 mmol), 2- 브로모페난트렌 (2-broiTK)phenanthrene) 대신 2-([1，1' :3'，1' '-terphenyl]一 3- y 1 ) -4-ch 1 or ο-6-pheny 1 - 1 , 3 , 5-t r i az i ne ( 16.0 g, 38.1 隱 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 71(15.8 g, 수율 59 %; MS:[M+H]+= 704) 을 제조하였다. Instead of compound P-6, instead of compound Q-26 (19.9 g, 38.1 mmol) and 2-bromophenanthrene (2-broiTK) phenanthrene) 2-([1,1 ': 3' ， 1 '' -terphenyl] 一3- y 1) Compound in the same manner as in Synthesis Example 1-1 except for using 4-ch 1 or ο-6-pheny 1-1, 3, 5-tri az i ne (16.0 g, 38.1 隱 ol) 71 (15.8 g, yield 59%; MS: [M + H] + = 704) was prepared.

Figure imgf000126_0002
Figure imgf000126_0002

Q-27  Q-27

4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-l,3,2- dioxaborolane(28.5 g, 80.4 mmol ) 대신 (4-(triphenylen_2ᅳ yDphenyOboronic acid(28.0 g, 80.4 誦 ol) 를 사용한 것 외에는 합성예 4-1과 동일한 방법으로 화합물 Q-27(27.4 g, 수율 62 %； MS:[M+H]+= 549) 을 제조하였다. 8의 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -l, 3,2-dioxaborolane (28.5 g, 80.4 mmol) instead of (4- (triphenylen_2 ᅳ yDphenyOboronic acid (28.0 g, 80.4 誦 ol ), Compound Q-27 (27.4 g, yield 62%; MS: [M + H] + = 549) was prepared in the same manner as in Synthesis Example 4-1. 8's

Figure imgf000127_0001
Figure imgf000127_0001

Q-27 Q-28  Q-27 Q-28

화합물 Q-5(25.0 g, 52.8 mmol) 대신 화합물 Q-27(29.0 g, 52.8 mmol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 Q-28(26.1 g, 수율 83 %； MS:[M+H]+= 597) 을 제조하였다. Compound Q-28 (26.1 g, yield 83%; MS: in the same manner as in Synthesis Example 4-2 except for using compound Q-27 (29.0 g, 52.8 mmol) instead of compound Q-5 (25.0 g, 52.8 mmol) [M + H] + = 597) was prepared.

Figure imgf000127_0002
Figure imgf000127_0002

화합물 P-6 .대산 화합물 Q-28U9.9 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromoplienanthrene) 대신 2-(4-chlorophenyl ^ S- diphenyl-HS-triazineaS.1 g, 38.1 醒 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 47(20.2 g, 수율 68 ； MS:[M+H]+= 778) 을 제조하였다. 합성예 16-1: 중간체 화합물 Q-29의 제조 Compound P-6. 2- (4-chlorophenyl ^ S-diphenyl-HS-triazineaS.1 g, 38.1 대신 instead of 2-acid compound Q-28U9.9 g, 38.1 mmol), 2-bromoplienanthrene Compound 47 (20.2 g, yield 68; MS: [M + H] + = 778) was prepared in the same manner as in Synthesis Example 1-1 except that ol was used. Synthesis Example 16-1 Preparation of Intermediate Compound Q-29

Figure imgf000128_0001
Figure imgf000128_0001

Q-29  Q-29

4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-l,3,2- d i oxabor o 1 ane ( 28.5 g, 80.4 mmol ) 대신 chr y s en-2-y 1 bor on i c acid(21.9 g, 80.4 腿 ol) 를 사용한 것 외에는 합성예 4-1과 동일한 방법으로 화합물 Q- 29(22.5 g, 수율 59 %； MS:[M+H]+= 473) 을 제조하였다. 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -l, 3,2-di oxabor o 1 ane (28.5 g, 80.4 mmol) instead of chr ys en-2-y 1 bor on ic Compound Q-29 (22.5 g, yield 59%; MS: [M + H] + = 473) was prepared in the same manner as in Synthesis Example 4-1, except that acid (21.9 g, 80.4 dl) was used.

Figure imgf000128_0002
Figure imgf000128_0002

화합물 Q_5(25.0 g, 52.8 mmol) 대신 화합물 Q-29(25.0 g, 52.8 mmol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 Q-30(23.9 g, 수율 87 %； MS:[M+H]+= 521) 을 제조하였다. 합성예 16-3: 화합물 51의 제조 Compound Q-30 (23.9 g, yield 87%; MS: [M] in the same manner as in Synthesis Example 4-2 except for using compound Q-29 (25.0 g, 52.8 mmol) instead of compound Q_5 (25.0 g, 52.8 mmol). + H] + = 521). Synthesis Example 16-3 Preparation of Compound 51

Figure imgf000129_0001
Figure imgf000129_0001

화합물 P-6 대신 화합물 Q-30(19.8 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-chloro-4— Compound Q-30 (19.8 g, 38.1 mmol) instead of compound P-6, 2-chloro-4 instead of 2-bromophenanthrene

(dibenzo[b , d] thiophen-2-yl )—6— phenyl— 1 ,3,5-tr iazine(14.2 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 51(17.0 g 수율 61 %； MS:[M+H]+= 732) 을 제조하였다. Compound 51 (17.0) in the same manner as in Synthesis Example 1-1, except that (dibenzo [b, d] thiophen-2-yl) —6— phenyl— 1, 3,5-tr iazine (14.2 g, 38.1 mmol) was used. g yield 61%; MS: [M + H] + = 732).

Figure imgf000129_0002
Figure imgf000129_0002

Q-31  Q-31

4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-l,3,2- d i oxabor o l ane (28.5 g, 80.4 mmol ) 대신 (3al,5al— dihydropyren— 1一 yDboronic acid(19.9 g, 80.4 mmol) 를 사용한 것 외에는 합성예 4—1과 동일한 방법으로 화합물 Q-3K22.8 g, 수율 63 %； MS:[M+H]+= 449) 을 제조하였다. 합성예 17-2: 중간체 화합물 Q-32의 제조 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -l, 3,2-di oxabor ol ane (28.5 g, 80.4 mmol) instead of (3al, 5al— dihydropyren— 1 一 yDboronic acid ( 29.9 g of compound Q-3K2, yield 63%; MS: [M + H] + = 449) was prepared in the same manner as in Synthesis example 4-1 except that 19.9 g, 80.4 mmol) was used. Synthesis Example 17-2 Preparation of Intermediate Compound Q-32

Figure imgf000130_0001
Figure imgf000130_0001

화합물 Q-5(25.0 g, 52.8 隱 ol) 대신 화합물 Q_31(23.7 g, 52.8 mmol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 Q-32(22.3 g, 수율 85 %； MS:[M+H]+= 497) 을 제조하였다. Compound Q-32 (22.3 g, yield 85%; MS: [] in the same manner as in Synthesis Example 4-2 except that compound Q_31 (23.7 g, 52.8 mmol) was used instead of compound Q-5 (25.0 g, 52.8 μL). M + H] + = 497).

Figure imgf000130_0002
Figure imgf000130_0002

화합물 P-6 대신 화합물 Q-32(18.9 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-chloro-4-(9,9-dimethyl-9H- f luoren— l—yl)—6— phenyl— 1，3,5— triazine(14.6 g, 38.1 匪 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 52(17.0 g, 수율 62 ； MS:[M+H]+= 718) 을 제조하였다. 합성예 18-1: 중간체 화합물 Q-33의 제조

Figure imgf000131_0001
Instead of compound P-6, compound Q-32 (18.9 g, 38.1 mmol), 2-chloro-4- (9,9-dimethyl-9H-f luoren— l—yl instead of 2-bromophenanthrene ) —6— phenyl— 1,3,5—triazine (14.6 g, 38.1 匪 ol), except that Compound 52 (17.0 g, yield 62; MS: [M + H] + = 718). Synthesis Example 18-1 Preparation of Intermediate Compound Q-33
Figure imgf000131_0001

Q-33  Q-33

4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-l,3,2- dioxaborolane(28.5 g, 80.4 mmol ) 대신 (3_tr itylphenyl )boronic acid(29.3 g, 80.4 mmol) 를 사용한 것 외에는 합성예 4—1과 동일한 방법으로 화합물 Q-33C27.3 g, 수율 60 %； MS:[M+H]+= 565) 을 제조하였다. 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -l, 3,2-dioxaborolane (28.5 g, 80.4 mmol) instead of (3_tr itylphenyl) boronic acid (29.3 g, 80.4 mmol) A compound Q-33C27.3 g, a yield of 60%; MS: [M + H] + = 565) was prepared in the same manner as in Synthesis example 4-1 except for the above.

Figure imgf000131_0002
Figure imgf000131_0002

Q-33 Q"34 Q-33 Q " 34

화합물 Q-5(25.0 g, 52.8 瞧 ol) 대신 화합물 Q-33(13.4 g, 52.8 隱 ol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 Q-34(28.1 g, 수율 87 ； MS:[M+H]+= 613) 을 제조하였다. Compound Q-34 (28.1 g, yield 87; MS) in the same manner as in Synthesis Example 4-2 except that compound Q-33 (13.4 g, 52.8 隱 ol) was used instead of compound Q-5 (25.0 g, 52.8 瞧 ol). : [M + H] + = 613).

Figure imgf000131_0003
브로모페난트렌 (2-bromophenanthrene) 대신 2— chloro-4-(9,9-dimethyl-9H- f luoren-4-yl )-6-phenyl-l,3,5— triazine(14.6 g, 38.1 隱 o 을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 56(20.3 g, 수율 64 %； MS:[M+H]+= 834) 을 제조하였다.
Figure imgf000131_0003
2—chloro-4- (9,9-dimethyl-9H- luluen-4-yl) -6-phenyl-l, 3,5— triazine (14.6 g, 38.1 대신 instead of 2-bromophenanthrene) A compound 56 (20.3 g, yield 64%; MS: [M + H] + = 834) was prepared in the same manner as in Synthesis Example 1-1 except that o was used.

Figure imgf000132_0001
Figure imgf000132_0001

Q-35  Q-35

4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-l,3,2- dioxaborolane(28.5 g, 80.4 mmol) 대신 [1， 1 ' :4'， 1 ' 1 -terphenyl ]-4- ylboronic acid(22.0 g, 80.4 隱 ol) 를 사용한 것 외에는 합성예 4-1과 동일한 방법으로 화합물 Q-35(21.0 g, 수율 55 %； MS:[M+H]+= 475) 을 제조하였다. 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -l, 3,2-dioxaborolane (28.5 g, 80.4 mmol) instead of [1, 1 ': 4', 1 ' 1 -terphenyl] Compound Q-35 (21.0 g, yield 55%; MS: [M + H] + = 475) was obtained in the same manner as in Synthesis Example 4-1 except that 4--4-ylboronic acid (22.0 g, 80.4 μl ol) was used. Prepared.

Figure imgf000132_0002
g, 수율 89 %; MS:[M+H]+= 523) 을 제조하였다.
Figure imgf000132_0002
g, yield 89%; MS: [M + H] + = 523).

Figure imgf000133_0001
Figure imgf000133_0001

화합물 P-6 대신 화합물 Q-36 19.9 g, 38.1 隱 ol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 4-chloro_2,6- diphenylpyrimidine(10.2 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 75(16.0 g, 수율 67 %; MS:[M+H]+= 627) 을 제조하였다. Example 1 Synthesis Example 1 except that 4-chloro_2,6-diphenylpyrimidine (10.2 g, 38.1 mmol) was used instead of compound Q-36 19.9 g, 38.1 隱 ol) and 2-bromophenanthrene. Compound 75 (16.0 g, yield 67%; MS: [M + H] + = 627) was prepared by the same method as -1.

Figure imgf000133_0002
Figure imgf000133_0002

R-1  R-1

1—브로모 -3-아이오도벤젠 (l-bromo-3-iodobenzene)(50 g, 176.7醒 ol) 2-브로모싸이오페놀 (2-Bromothiophenol)(40.1 g, 212.0 mmol) 을 에탄을 (EtOH) 500ml에 분산시키고 Na0H(9.2g, 229.7 mmol) 을 넣은 뒤， 6시간동안 환류시켰다. 반응이 종료된 후 상은으로 식히고， 물을 넣고 추출하여 얻은 유기층을 감압증류한 흔합물을 시리카겔에 필터하여 화합물 R-K48.6 g, 수율 80 %； MS:[M+H]+= 342) 을 제조하였다. .

Figure imgf000134_0001
화합물 R-U40.0 g, 116.3 mmol)을 다이클로로메탄 (DCM) 500 ml에 녹인 뒤， DDQ(2,3-dichloro— 5,6ᅳ dicyano-1,4— berizoquinone)(31.6 g, 140.0 隱 ol)을 넣고 상온에서 24시간동안 교반하였다. 반응이 종료된 후 과량의 물을 이용하여 3회 추출한다. 유기층을 황산마그네슘 (magnesium sulfate)로 건조한 뒤 감압증류하여 얻은 흔합물을 숏컬럼으로 정제하여 화합물 R- 2(21.7 g, 수율 71 %; MS:[M+H]+= 262) 을 제조하였다. 1—Bromo-3-iodobenzene (50 g, 176.7) ol) 2-Bromothiophenol (40.1 g, 212.0 mmol) was added ethane (EtOH ) Dispersed in 500ml, added Na0H (9.2g, 229.7 mmol), and refluxed for 6 hours. After the reaction was completed, the mixture was cooled to silver, extracted with water, and the extracted organic layer was filtered under reduced pressure. The mixture was filtered through a silica gel to give a compound R-K48.6 g, a yield of 80%; MS: [M + H] + = 342 ) Was prepared. .
Figure imgf000134_0001
Compound R-U40.0 g, 116.3 mmol) was dissolved in 500 ml of dichloromethane (DCM), followed by DDQ (2,3-dichloro— 5,6 ᅳ dicyano-1,4— berizoquinone) (31.6 g, 140.0 隱). ol) was added and stirred at room temperature for 24 hours. After the reaction is completed, the resultant is extracted three times with excess water. The organic layer was dried over magnesium sulfate, and the mixture obtained by distillation under reduced pressure was purified by a shot column to obtain Compound R-2 (21.7 g, Yield 71%; MS: [M + H] + = 262).

Figure imgf000134_0002
Figure imgf000134_0002

R-2 R-3  R-2 R-3

화합물 R-2(20 g, 76.0 匪 ol)을 테트라하이드로퓨란 (250 ml)에 녹인 후， -78°C로 온도를 낮추고 1.7 M 터셔리-부틸리튬 (t-BuLi)(44.7 ml, 76.0 mmol)을 천천히 가하였다. 동일 온도에서 한 시간 동안 교반한 후 트리아이소프로필보레이트 (B(0iPr)3)(20.1 ml, 152.0 隱 ol)을 가하고， 상온으로 온도를 서서히 을리면서 3시간동안 교반하였다. 반웅 흔합물에 2 N 염산수용액 (100 ml)을 가하고 1.5 시간 동안 상온에서 교반하였다. 생성된 침전물을 거르고 물과 에틸에테르 (ethyl ether)로 차례로 씻은 후 진공 건조하였다. 건조 후 에틸에테르에 분산시켜 두 시간 동안 교반한 후 여과하고 건조하여 화합물 R-3CL5.1 g, 수율 87 %; MS: [M+H]+=229)을 제조하였다. Compound R-2 (20 g, 76.0 μL) was dissolved in tetrahydrofuran (250 ml), then the temperature was lowered to -78 ° C and 1.7 M tert-butyllithium (t-BuLi) (44.7 ml, 76.0 mmol ) Was added slowly. After stirring for 1 hour at the same temperature, triisopropylborate (B (0iPr) 3 ) (20.1 ml, 152.0 Pa ol) was added and stirred for 3 hours while slowly cooling the temperature to room temperature. To the reaction mixture was added 2N aqueous hydrochloric acid solution (100 ml) and stirred at room temperature for 1.5 hours. The resulting precipitate was filtered off, washed sequentially with water and ethyl ether, and dried in vacuo. After drying, the mixture was dispersed in ethyl ether, stirred for 2 hours, filtered and dried to obtain compound R-3CL5.1 g, yield 87%; MS: [M + H] + = 229).

Figure imgf000135_0001
화합물 R-3 15.0 g, 65.8 mmol)과 2-ch lor c)-4,6-di phenyl -1， 3,5- triazine(17.6 g, 162.3 mmol)을 테트라하이드로퓨란 (200 ml)에 분산시킨 후， 2M 탄산칼륨수용액 (aq. K2C03)(98.7 ml, 197.4 mmol)을 첨가하고 테트라키스트리페닐포스피노팔라듐 [Pd(PPh3)4](1.5 g, 2 mol%)을 넣은 후 5시간 동안 교반 환류하였다. 상은으로 온도를 낮추고 생성된 고체를 여과하였다. 여과된 고체를 테트라하이드로퓨란과 에틸아세테이트로 재결정하고 여과한 뒤， 건조하여 화합물 R-4(24.1 g, 수율 88 %； MS:[M+H]+=416)를 제조하였다.
Figure imgf000135_0001
Compound R-3 15.0 g, 65.8 mmol) and 2-chlor c) -4,6-diphenyl-1,3,5-triazine (17.6 g, 162.3 mmol) were dispersed in tetrahydrofuran (200 ml). 2M aqueous potassium carbonate solution (aq. K 2 C0 3 ) (98.7 ml, 197.4 mmol) was added and tetrakistriphenylphosphinopalladium [Pd (PPh 3 ) 4 ] (1.5 g, 2 mol%) was added thereto. Stirring to reflux for 5 hours. The temperature was lowered with phase silver and the resulting solid was filtered off. The filtered solid was recrystallized with tetrahydrofuran and ethyl acetate, filtered and dried to give compound R-4 (24.1 g, yield 88%; MS: [M + H] + = 416).

Figure imgf000135_0002
Figure imgf000135_0002

화합물 R-4(40 g, 96.3 mmol)을 클로로포름 (350mL)에 녹이고， 아세트산 (350mL)을 첨가한 후， 0°C하에서 Br2(5.2 mL, 101.1 mmol)을 적가하였다. 얻어진 흔합물을 상온으로 올려 5시간 동안 교반시킨다. 반웅이 종료 된 후 반응액을 농축시키고 에탄을로 재결정하여 화합물 R- 5(34.3 g, 수율 72 %; MS:[M+H]+=494)를 제조하였다. Compound R-4 (40 g, 96.3 mmol) was dissolved in chloroform (350 mL), acetic acid (350 mL) was added, and Br 2 (5.2 mL, 101.1 mmol) was added dropwise at 0 ° C. The obtained mixture is raised to room temperature and stirred for 5 hours. After the reaction was completed, the reaction solution was concentrated and recrystallized with ethane to give Compound R-5 (34.3 g, Yield 72%; MS: [M + H] + = 494).

Figure imgf000136_0001
Figure imgf000136_0001

화합물 R-5(40 g, 80.9 mmol) 비스 (피나콜라토)디보론 (Bis(pinacolato)diborone)(24.7 g,97.1 瞧 ol) 포타슘아세테이트 (potassium acetate)(33.5 g, 242.7 mmol), 테트라키스트리페닐포스피노팔라듐 (0) [Pd(PPh3)4](1.9 g, 2 mol¾>)을 테트라하이드로퓨란 (500 ml) 에 넣고 12시간 동안 환류시켰다. 반웅이 종료된 후 상온으로 식힌 뒤 감압 증류하여 용매를 제거하였다. 이것을 클로로포름 (Chloroform)에 녹이고 물로 3회 씻어낸 뒤 유기층을 분리하여 황산 마그네슴 (Magnesium sulfate)으로 건조하였다. 이를 감압 증류하여 화합물 R-6(39.9 g, 수율 91 %； MS: [M+H]+=542)을 제조하였다. Compound R-5 (40 g, 80.9 mmol) bis (pinacolato) diborone (24.7 g, 97.1 瞧 ol) potassium acetate (33.5 g, 242.7 mmol), tetrakis Triphenylphosphinopalladium (0) [Pd (PPh 3 ) 4 ] (1.9 g, 2 mol¾>) was added to tetrahydrofuran (500 ml) and refluxed for 12 hours. After the reaction was completed, the reaction mixture was cooled to room temperature and then distilled under reduced pressure to remove the solvent. This was dissolved in chloroform, washed three times with water, and the organic layer was separated and dried over magnesium sulfate. This was distilled under reduced pressure to obtain compound R-6 (39.9 g, yield 91%; MS: [M + H] + = 542).

Figure imgf000136_0002
Figure imgf000136_0002

화합물 P-6 대신 화합물 R-6(20.6 g, 38.1 mmol), 2- 브로모페난트렌 (2— bromophenanthrene) 대신 3-bromof luoranthene( 10.7 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 5(17.9 g, 수율 76 %； MS: [M+H]+= 616) 을 제조하였다. 합성예 20-2: 화합물 53의 제조 Synthesis Example 1-1 except that Compound R-6 (20.6 g, 38.1 mmol) instead of Compound P-6 and 3-bromof luoranthene (10.7 g, 38.1 mmol) were used instead of 2-bromophenanthrene. In the same manner, compound 5 (17.9 g, yield 76%; MS: [M + H] + = 616) was prepared. Synthesis Example 20-2: Preparation of Compound 53

Figure imgf000137_0001
Figure imgf000137_0001

화합물 P-6 대신 화합물 R-6(20.6 g' 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 3-(6-bromonaphthalen-2- yl)phenanthrene(14.6 g, 38.1 mmol)을 사용한 것 외에는 합성예 1—1과 동일한 방법으로 화합물 53(18.9 g, 수율 69 %； MS:[M+H]+= 718) 을 제조하였다. Using compound R-6 (20.6 g '38.1 mmol) instead of compound P-6, 3- (6-bromonaphthalen-2-yl) phenanthrene (14.6 g, 38.1 mmol) instead of 2-bromophenanthrene A compound 53 (18.9 g, yield 69%; MS: [M + H] + = 718) was prepared in the same manner as in Synthesis Example 1-1 except for the above.

Figure imgf000137_0002
Figure imgf000137_0002

2-ch 1 or 0-4 , 6-di pheny 1 -1 , 3 , 5-t r i az ine ( 17.6 g' 162.3 mmol) 대신 2- ( [ 1， 1 '— b i pheny 1 ] -2-yl )—4_ch 1 or o_6— pheny 1— l,3,5—triazine(55.8 g, 162.3 mmol) 을 사용한 것 외에는 합성예 20 의 화합물 R-4의 제조법과 동일한 방법으로 화합물 S-K68.6 g, 수율 86 %； MS:[M+H]+= 492) 을 제조하였다. 2-ch 1 or 0-4, 6-di pheny 1 -1, 3, 5-tri az ine (17.6 g '162.3 mmol) instead of 2- ([1 ， 1' — bi pheny 1] -2-yl) —4_ch 1 or o_6—pheny 1—l, 3,5—triazine (55.8 g, 162.3 mmol) except that S-K68.6 g, yield was obtained in the same manner as in the preparation of Compound R-4 of Synthesis Example 20. 86%; MS: [M + H] + = 492) was prepared.

Figure imgf000138_0001
화합물 R_4(40 g, 96.3 mmol) 대신 화합물 S-l(47.3 g, 96.3隱 ol)을 사용한 것 외에는 합성예 20 의 화합물 R-5의 제조법과 동일한 방법으로 화합물 S_2(50.5 g, 수율 92 %； MS:[M+H]+= 492) 을 제조하였다.
Figure imgf000138_0001
Compound S_2 (50.5 g, yield 92%; MS :) in the same manner as in the preparation of compound R-5 of Synthesis Example 20 except for using the compound Sl (47.3 g, 96.3 mmol) in place of the compound R_4 (40 g, 96.3 mmol). [M + H] + = 492) was prepared.

Figure imgf000138_0002
Figure imgf000138_0002

화합물 73  Compound 73

화합물 P-6 대신 화합물 S-2(20.6 g, 38.1 隱 ol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 [.1，1' :4'，1' '-terphenyl]-2'— ylboronic acid(10.4 g, 38.1 瞧 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 78(14.8 g, 수율 54 ； MS:[M+H]+= 720) 을 제조하였다. 합성예 22: 중간체 화합물 S-4의 제조 [.1,1 ': 4' ， 1 '' -terphenyl] -2'—in place of compound S-2 (20.6 g, 38.1 隱 ol) and 2-bromophenanthrene instead of compound P-6 Compound 78 (14.8 g, yield 54; MS: [M + H] + = 720) was prepared in the same manner as in Synthesis Example 1-1 except for using ylboronic acid (10.4 g, 38.1 Pa). Synthesis Example 22 Preparation of Intermediate Compound S-4

Figure imgf000139_0001
Figure imgf000139_0001

2-ch 1 or 0-4 , 6-di pheny 1 -1 , 3 , 5-t r i az i ne ( 17.6 g, 162.3 隱 ol) 대신 2- ( [ 1， 1 ' -b i pheny 1 ] -3-y 1 ) -4-ch 1 oro-6-pheny 1-1,3,5-tr iazine(55.8 g， 162.3 匪 ol) 을 사용한 것 외에는 합성예 20 의 화합물 R-4의 제조법과 동일한 방법으로 화합물 S-3(71.0 g, 수율 89 %; MS:[M+H]+= 492) 을 제조하였다. 2-ch 1 or 0-4, 6-di pheny 1 -1, 3, 5-tri az i ne (17.6 g, 162.3 隱 ol) instead of 2- ([1, 1 '-bi pheny 1] -3- y 1) Compound in the same manner as in the preparation of Compound R-4 of Synthesis Example 20 except for using 4-ch 1 oro-6-pheny 1-1,3,5-tr iazine (55.8 g, 162.3 匪 ol) S-3 (71.0 g, yield 89%; MS: [M + H] + = 492) was prepared.

Figure imgf000139_0002
Figure imgf000139_0002

화합물 R-4(40 g, 96.3隱 ol) 대신 화합물 S-3(47.3 g, 96.3隱 ol)을 사용한 것 외에는 합성예 20 의 화합물 R— 5의 제조법과 동일한 방법으로 화합물 S-4(49.4 g, 수율 90 %； MS:[M+H]+= 570) 을 제조하였다. 합성예 22-1: 화합물 79의 제조 Compound S-4 (49.4 g) in the same manner as in the preparation of Compound R-5 of Synthesis Example 20, except that Compound S-3 (47.3 g, 96.3 'ol) was used instead of Compound R-4 (40 g, 96.3' ol). , Yield 90%; MS: [M + H] + = 570) was prepared. Synthesis Example 22-1: Preparation of Compound 79

Figure imgf000140_0001
Figure imgf000140_0001

화합울 79  Harmony Wool 79

화합물 P-6 대신 화합물 S-4(21.7 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 (4'-phenyl-[l, 1'：3'，1' '- terphenyl]-4-yl)boronic acid(13.3 g, 38.1 誦 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 79(20.6 g, 수율 68 %; MS:[M+H]+= 796) 을 제조하였다. Instead of compound P-6 compound 4-4 (21.7 g, 38.1 mmol), 2-bromophenanthrene (2-bromophenanthrene) (4'-phenyl- [l, 1 ': 3' ， 1 ''-terphenyl] Compound 79 (20.6 g, yield 68%; MS: [M + H] + = 796) was obtained in the same manner as in Synthesis Example 1-1 except for using -4-yl) boronic acid (13.3 g, 38.1 μl). Prepared.

Figure imgf000140_0002
Figure imgf000140_0002

2-chloro-4,6-diphenyl-l,3,5-triazine(17.6 g, 162.3 mmol) 대신 2- chloro-4,6-diphenylpyrimidine(43.3 g, 162.3 mmol) 을 사용한 것 외에는 합성예 20 의 화합물 R-4의 제조법과 동일한 방법으로 화합물 S-5(57.9 g, 수율 86 %； MS:[M+H]+= 415) 을 제조하였다. Compound of Synthesis Example 20 except for using 2-chloro-4,6-diphenylpyrimidine (43.3 g, 162.3 mmol) instead of 2-chloro-4,6-diphenyl-l, 3,5-triazine (17.6 g, 162.3 mmol) Compound S-5 (57.9 g, yield 86%; MS: [M + H] + = 415) was prepared in the same manner as in the preparation of R-4.

Figure imgf000141_0001
Figure imgf000141_0001

화합물 R_4(40 g, 96.3 mmol) 대신 화합물 S-3(39.9 g, 96.3醒 ol)을 사용한 것 외에는 합성예 20 의 화합물 R-5의 제조법과 동일한 방법으로 화합물 Sᅳ 6(41.3 g, 수율 87 %； MS:[M+H]+= 493) 을 제조하였다. Compound S '6 (41.3 g, yield 87) in the same manner as in the preparation of Compound R-5 of Synthesis Example 20, except that Compound S-3 (39.9 g, 96.3' ol) was used instead of Compound R_4 (40 g, 96.3 mmol). %; MS: [M + H] + = 493).

Figure imgf000141_0002
Figure imgf000141_0002

화합물 P-6 대신 화합물 S-6U8.8 g, 38.1 匪 ol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 [1，1' :3' ,1' ' :3' ' ,1' 1 '- quaterphenyl]-4-ylboronic acid(13.3 g, 38.1 隱 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 43(18.4 g, 수율 67 ； MS:[M+H]+= 719) 을 제조하였다. 합성예 23-2: 화합물 80의 제조 Compound S-6U8.8 g, 38.1 g ol) instead of 2-bromophenanthrene, instead of compound P-6 [1，1 ': 3', 1 '': 3 '', 1 ' 1 Compound 43 (18.4 g, yield 67; MS: [M + H] + = 719) in the same manner as in Synthesis Example 1-1 except for using '-quaterphenyl] -4-ylboronic acid (13.3 g, 38.1 隱 ol)' Was prepared. Synthesis Example 23-2: Preparation of Compound 80

Figure imgf000142_0001
Figure imgf000142_0001

화합물 P-6 대신 화합물 S-6(18.8 g, 38.1 隱 ol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 [1， 1' :2'， 1' ' :4' 1 , 1' ' quaterphenyl]-4' ' '-ylboronic acid(13.3 g, 38.1 mm이)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 80(17.8 g, 수율 65 %; MS:[M+H]+= 719) 을 제조하였다. Instead of compound P-6, instead of compound S-6 (18.8 g, 38.1 隱 ol) and 2-bromophenanthrene, [1, 1 ': 2', 1 '': 4 ' 1 , 1'' quaterphenyl] -4 '''-Compound 80 (17.8 g, yield 65%; MS: [M + H] + = in the same manner as in Synthesis Example 1-1, except that' -ylboronic acid (13.3 g, 38.1 mm) 'was used 719) was prepared.

Figure imgf000142_0002
Figure imgf000142_0002

S-7  S-7

2-ch 1 or 0-4 , 6-d i heny l-l,3,5-triazine(17.6 g, 162.3醒 ol) 대신 2- (4-chl oropheny 1 )-4-(dibenzo[b,d]thi ophen— 2— y 1 ) -6-pheny 1-1,3,5- triazine(73.0 g, 162.3 mmol) 을 사용한 것 외에는 합성예 20 의 화합물 R— 4의 제조법과 동일한 방법으로 화합물 S-7(80.5 g, 수율 83 %； MS:[M+H]+= 598) 을 제조하였다. 2- (4-chl oropheny 1) -4- (dibenzo [b, d] thi ophen instead of 2-ch 1 or 0-4, 6-di heny ll, 3,5-triazine (17.6 g, 162.3 醒 ol) — 2— y 1) Compound S-7 (80.5) in the same manner as in the preparation of Compound R-4 of Synthesis Example 20, except that 6-pheny 1-1,3,5-triazine (73.0 g, 162.3 mmol) was used. g, yield 83%; MS: [M + H] + = 598) was prepared.

Figure imgf000143_0001
Figure imgf000143_0001

S-7 S-8  S-7 S-8

화합물 R_4(40 g, 96.3 mmol) 대신 화합물 S_7(57.6 g, 96.3 匪 ol)을 사용한 것 외에는 합성예 20 의 화합물 R-5의 제조법과 동일한 방법으로 화합물 S-8(52.8 g, 수율 81 %； MS:[M+H]+= 676) 을 제조하였다. Compound S-8 (52.8 g, yield 81%) in the same manner as in the preparation of compound R-5 of Synthesis Example 20, except that compound S_7 (57.6 g, 96.3 mmol) was used instead of compound R_4 (40 g, 96.3 mmol); MS: [M + H] + = 676).

Figure imgf000143_0002
Figure imgf000143_0002

화합물 P-6 대신 화합물 S-8(18.8 g, 38.1 隱 ol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 4,4,5,5-tetramethyl-2-(10_ pheny 1 henant hr en-9-y l)-l,3,2-dioxaborol ane (14.5 g, 38.1 匪 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 18(17.5 g, 수율 54 %； MS:[M+H]+= 850) 을 제조하였다. 합성예 25: 중간체 화합물 S-10의 제조 Instead of compound P-6, compound S-8 (18.8 g, 38.1 隱 ol), 2-bromophenanthrene instead of 4,4,5,5-tetramethyl-2- (10_pheny 1 henant hr en- Compound 18 (17.5 g, yield 54%; MS: [M + H] in the same manner as in Synthesis Example 1-1 except for using 9-yl) -l, 3,2-dioxaborol ane (14.5 g, 38.1 μl ol) ] + = 850). Synthesis Example 25 Preparation of Intermediate Compound S-10

Figure imgf000144_0001
Figure imgf000144_0001

S-9  S-9

2-ch 1 or 0-4 , 6-d i phenyl -1 , 3 , 5-t r i az i ne ( 17.6 g, 162.3 mmol) 대신 2- chloro— 4— (dibenz이 b,d] furan-l-yl )—6— phenyl— 1,3,5— triazine(58.1 g, 162.3 mmol) 을 사용한 것 외에는 합성예 20 의 화합물 R-4의 제조법과 동일한 방법으로 화합물 S-9(71.4 g， 수율 87 %； MS:[M+H]+= 506) 을 제조하였다. 2- chloro— 4— (dibenz b, d] furan-l-yl instead of 2-ch 1 or 0-4, 6-di phenyl -1, 3, 5-tri az i ne (17.6 g, 162.3 mmol) ) -6—phenyl- 1,3,5- triazine (58.1 g, 162.3 mmol), except for using Compound S-9 (71.4 g, yield 87%; MS: [M + H] + = 506).

Figure imgf000144_0002
화합물 R-4(40 g, 96.3隱 ol) 대신 화합물 S— 9(48.7 g, 96.3瞧 ol)을 사용한 것 외에는 합성예 20 의 화합물 R-5의 제조법과 동일한 방밥으로 화합물 S-10 6.2 g, 수율 82 %； MS:[M+H]+= 584) 을 제조하였다. 합성예 25-1: 화합물 20의 제조
Figure imgf000144_0002
Compound S-10 6.2 g, in the same manner as in the preparation of Compound R-5 of Synthesis Example 20, except that Compound S-9 (48.7 g, 96.3 µl) was used instead of Compound R-4 (40 g, 96.3 µl) Yield 82%; MS: [M + H] + = 584). Synthesis Example 25-1: Preparation of Compound 20

Figure imgf000145_0001
Figure imgf000145_0001

5-10  5-10

화합울 20  Harmony Wool 20

화합물 P-6 대신 화합물 S-10(34.5 g, 38.1 隱 ol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 t r i pheny 1 en-2-y 1 bor on i c acid(10.4 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 20(18.7 g, 수율 67 %； MS: [M+H]+= 732) 을 제조하였다. Compound S-10 instead of compound P-6 (34.5 g, 38.1 P ol), tri pheny 1 en-2-y 1 bor on ic acid (10.4 g, 38.1 mmol) instead of 2-bromophenanthrene A compound 20 (18.7 g, yield 67%; MS: [M + H] + = 732) was prepared in the same manner as in Synthesis Example 1-1 except for using.

Figure imgf000145_0002
Figure imgf000145_0002

2-chloro-4,6-diphenyl-l,3,5-triazine(17.6 g, 162.3 腿 ol) 대신 2- ([l,l'-biphenyl]-4-yl-2'，3' ,4' ,5' ,6'-d5)-4-chloro-6- phenylpyrimidine(56.5 g, 162.3 瞧 ol) 을 사용한 것 외에는 합성예 20 의 화합물 R-4의 제조법과 동일한 방법으로 화합물 S= 1(71.6 g, 수율 89 ； MS: [M+H]+= 496) 을 제조하였다. 2- ([l, l'-biphenyl] -4-yl-2 '， 3', 4 'instead of 2-chloro-4,6-diphenyl-l, 3,5-triazine (17.6 g, 162.3 腿 ol) Compound S = 1 (71.6 g) in the same manner as in the preparation of Compound R-4 of Synthesis Example 20 except for using, 5 ', 6'-d5) -4-chloro-6-phenylpyrimidine (56.5 g, 162.3 瞧 ol) , Yield 89; MS: [M + H] + = 496).

Figure imgf000146_0001
Figure imgf000146_0001

화합물 R-4(40 g, 96.3 mmol) 대신 화합물 S-ll(47.7 g, 96.3 mmol)을 사용한 것 외에는 합성예 20 의 화합물 R-5의 제조법과 동일한 방법으로 화합물 S-12(47.0 g, 수율 85 %； MS:[M+H]+= 574) 을 제조하였다. Compound S-12 (47.0 g, yield) in the same manner as in the preparation of compound R-5 of Synthesis Example 20 except that Compound S-ll (47.7 g, 96.3 mmol) was used instead of Compound R-4 (40 g, 96.3 mmol) 85%; MS: [M + H] + = 574) was prepared.

Figure imgf000146_0002
Figure imgf000146_0002

화합물 P-6 대신 화합물 S—12(21.9 g, 38.1 mmol), 2- 브로모페난트렌 (2_bromophenanthrene) 대신 t r i pheny 1 en-2-y 1 bor on i c acid(10.4 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 24(19.5 g, 수율 71 %； MS:[M+H]+= 722) 을 제조하였다. 합성예 27-1: 중간체 화합물 Q-37의 제조 Use of compound S—12 (21.9 g, 38.1 mmol) instead of compound P-6, tri pheny 1 en-2-y 1 bor on ic acid (10.4 g, 38.1 mmol) instead of 2-bromophenanthrene Otherwise, Compound 24 (19.5 g, yield 71%; MS: [M + H] + = 722) was prepared in the same manner as in Synthesis Example 1-1. Synthesis Example 27-1 Preparation of Intermediate Compound Q-37

Figure imgf000147_0001
Figure imgf000147_0001

Q-37  Q-37

4,4,5,5-tetramethyl-2-(triphenylen-2-yl)-l,3,2- d i oxabor o 1 ane (28.5 g, 80.4 mmol ) 대신 (3— (tr iphenylsi lyl )phenyl )boronic acid(30.6 g, 80.4 mmol) 를 사용한 것 외에는 합성예 4-1과 동일한 방법으로 화합물 Q-37(30.6 g, 수율 60 %； MS:[M+H]+= 581) 을 제조하였다. 4,4,5,5-tetramethyl-2- (triphenylen-2-yl) -l, 3,2-di oxabor o 1 ane (28.5 g, 80.4 mmol) instead of (3— (tr iphenylsi lyl) phenyl) boronic Compound Q-37 (30.6 g, yield 60%; MS: [M + H] + = 581) was prepared in the same manner as in Synthesis Example 4-1, except that acid (30.6 g, 80.4 mmol) was used.

Figure imgf000147_0002
Figure imgf000147_0002

화합물 Q— 5(25.0 g, 52.8 匪 ol) 대신 화합물 Q— 37(30.7 g, 52.8 mmol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 Q-38(28.5 g， 수율 86 %； MS:[M+H]+= 629) 을 제조하였다. Compound Q-38 (28.5 g, yield 86%; MS in the same manner as in Synthesis Example 4-2 except for using compound Q-37 (30.7 g, 52.8 mmol) instead of compound Q-5 (25.0 g, 52.8 匪 ol) : [M + H] + = 629).

Figure imgf000147_0003
Figure imgf000147_0003

화합물 P-6 대신 화합물 Q-38(24.0 g, 38.1 瞧 o 브로모페난트렌 (2-bromophenanthrene) 대신 2-chloro— 4-Compound Q-38 (24.0 g, 38.1 瞧 o instead of compound P-6) 2-chloro- 4- instead of 2-bromophenanthrene

(dibenzo[b,d]thi ophen-2-y 1 ) -6-pheny I— 1,3,5— triazine (14.2 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 38(19.2 g, 수율 60 %； MS:[M+H]+= 840) 을 제조하였다. Compound 38 in the same manner as in Synthesis Example 1-1 except for using (dibenzo [b, d] thi ophen-2-y 1) -6-pheny I— 1,3,5— triazine (14.2 g, 38.1 mmol). (19.2 g, yield 60%; MS: [M + H] + = 840) was prepared.

Figure imgf000148_0001
Figure imgf000148_0001

S-13 S-13

2-ch 1 or 0-4 , 6-di phenyl -1 , 3 , 5-t r i az i ne ( 17.6 g, 162.3 隱 ol) 대신 2- chloro-4-(di benzo [b,d] furan-3-yl )— 6— phenyl—l,3,5—triazine(58.1 g, 162.3 mmol) 을 사용한 것 외에는 합성예 20 의 화합물 R-4의 제조법과 동일한 방법으로 화합물 S-13(71.4 g, 수율 87 %； MS:[M+H]+= 506) 을 제조하였다. 2- chloro-4- (di benzo [b, d] furan-3 instead of 2-ch 1 or 0-4, 6-di phenyl -1, 3, 5-tri az i ne (17.6 g, 162.3 隱 ol) Compound S-13 (71.4 g, yield 87) in the same manner as in the preparation of Compound R-4 of Synthesis Example 20, except that -yl) -6-phenyl-l, 3,5-triazine (58.1 g, 162.3 mmol) was used. %; MS: [M + H] + = 506) was prepared.

Figure imgf000148_0002
Figure imgf000148_0002

S-13  S-13

S-14  S-14

화합물 R-4(40 g, 96.3 隱 ol) 대신 화합물 S-13(48.7 g, 96.3 mmol)을 사용한 것 외에는 합성예 20 의 화합물 R-5의 제조법과 동일한 방법으로 화합물 S-14(50.1 g, 수율 89 %； MS:[M+H]+= 584) 을 제조하였다.

Figure imgf000149_0001
Except for using the compound S-13 (48.7 g, 96.3 mmol) instead of compound R-4 (40 g, 96.3 隱 ol) and the compound S-14 (50.1 g, Yield 89%; MS: [M + H] + = 584).
Figure imgf000149_0001

S-14 &합물 41  S-14 & Compound 41

화합물 P-6 대신 화합물 S-14(21.9 g, 38.1 圆 ol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 [1，1' :2'，1' '-terphenyl]-3- ylboronic acid(10.4 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 41(19.3 g, 수율 69 %; MS:[M+H]+= 734) 을 제조하였다. Instead of compound P-6, instead of compound S-14 (21.9 g, 38.1 圆 ol) and 2-bromophenanthrene, [1,1 ': 2' ， 1 '' -terphenyl] -3-ylboronic acid Compound 41 (19.3 g, yield 69%; MS: [M + H] + = 734) was prepared in the same manner as in Synthesis Example 1-1 except for using (10.4 g, 38.1 mmol).

Figure imgf000149_0002
Figure imgf000149_0002

2-chloro-4,6-diphenyl-l,3,5-triazine(17.6 g, 162.3匪 ol) 대신 2- ch 1 oro-4- ( d i benzo [b,d]thi ophen-4-y 1 )—6— pheny 1-1,3,5-tr iazine(60.7 g, 162.3 隱 ol) 을 사용한 것 외에는 합성예 20 의 화합물 R-4의 제조법과 동일한 방법으로 화합물 S_15(78.7 g, 수율 93 %； MS:[M+H]+= 522) 을 제조하였다. 2-ch 1 oro-4- (di benzo [b, d] thi ophen-4-y 1) instead of 2-chloro-4,6-diphenyl-l, 3,5-triazine (17.6 g, 162.3 匪 ol) —6— Compound S_15 (78.7 g, yield 93%) in the same manner as in the preparation of Compound R-4 of Synthesis Example 20 except for using pheny 1-1,3,5-tr iazine (60.7 g, 162.3 隱 ol); MS: [M + H] + = 522).

Figure imgf000150_0001
Figure imgf000150_0001

화합물 R-4(40 g, 96.3 mmol) 대신 화합물 S-15(50.2 g, 96.3 mmol)을 사용한 것 외에는 합성예 20 의 화합물 R-5의 제조법과 동일한 방법으로 화합물 S_16(50.3 g, 수율 87 ； MS:[M+H]+= 600) 을 제조하였다. Compound S_16 (50.3 g, yield 87; in the same manner as in the preparation of compound R-5 of Synthesis Example 20, except that compound S-15 (50.2 g, 96.3 mmol) was used instead of compound R-4 (40 g, 96.3 mmol). MS: [M + H] + = 600).

Figure imgf000150_0002
Figure imgf000150_0002

화합물 P-6 대신 화합물 S-16(22.9 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 [1，1' :3'，1' '—terphenyl]— 3- ylboronic acid(10.4 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 42(20.6 g, 수율 72 %； MS:[M+H]+= 750) 을 제조하였다. 합성예 30: 화합물 23의 제조 Instead of compound P-6, instead of compound S-16 (22.9 g, 38.1 mmol) and 2-bromophenanthrene, [1,1 ': 3' ， 1 '' —terphenyl] — 3-ylboronic acid ( Compound 42 (20.6 g, yield 72%; MS: [M + H] + = 750) was prepared in the same manner as in Synthesis Example 1-1 except that 10.4 g, 38.1 mmol) was used. Synthesis Example 30 Preparation of Compound 23

Figure imgf000151_0001
Figure imgf000151_0001

화합물 6(20 g, 28.5隱 ol)을 테트라하이드로퓨란 (500 ml)에 녹인 후， -78 °C 로 온도를 낮추고 1.7 M 터셔리-부틸리륨 (t-BuLi)(16.8 ml, 28.5 隱 ol)을 천천히 가하였다. 동일 온도에서 한 시간 동안 교반한 후 과량의 0를 적가하여 반응을 종료시킨다. 상온으로 온도를 서서히 올리고, 유기층을 분리한 뒤 황산마그네슘으로 건조하여 감압증류한다. 얻어진 흔합물을 컬럼크로마토그래피를 이용하여 핵산 /에틸아세테이트 (10:1)로 정제하여 화합물 23(9.6 g, 수율 48 ； MS:[M+H]+= 703)을 제조하였다. After dissolving compound 6 (20 g, 28.5 μl) in tetrahydrofuran (500 ml), the temperature was lowered to -78 ° C and 1.7 M tert-butyllilium (t-BuLi) (16.8 ml, 28.5 μl ol). ) Was added slowly. After stirring for one hour at the same temperature, an excess of zero is added dropwise to terminate the reaction. The temperature is gradually raised to room temperature, the organic layer is separated, dried over magnesium sulfate, and distilled under reduced pressure. The obtained mixture was purified by nucleic acid / ethyl acetate (10: 1) using column chromatography to give compound 23 (9.6 g, yield 48; MS: [M + H] + = 703).

Figure imgf000151_0002
Figure imgf000151_0002

화합물 6 대신 화합물 8(20.4 g, 28.5 瞧 ol), 1.7 M 터셔리- 부틸리튬 (t-BuLi)(33.5 ml, 57.0 瞧 ol) 을 사용한 것 외에는 합성예 30과 동일한 방법으로 화합물 60(8.6 g, 수율 42 %； MS:[M+H]+= 718) 을 제조하였다. 합성예 32-1: 중간체 화합물 Q-39의 제조 Compound 60 (8.6 g) in the same manner as in Synthesis Example 30, except that Compound 8 (20.4 g, 28.5 μl ol) and 1.7 M tert-butyllithium (t-BuLi) (33.5 ml, 57.0 μl ol) were used instead of Compound 6. , Yield 42%; MS: [M + H] + = 718) was prepared. Synthesis Example 32-1: Preparation of Intermediate Compound Q-39

Figure imgf000152_0001
Figure imgf000152_0001

화합물 P-6 대신 화합물 Q-36(19.9 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-(4-chlorophenyl ^A^- diphenyl-l^.S-triazine lS.1 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 Q-39(22.0 g, 수율 82 %; MS:[M+H]+= 704) 을 제조하였다. Compound Q-36 (19.9 g, 38.1 mmol) instead of compound P-6, 2- (4-chlorophenyl ^ A ^ -diphenyl-l ^ .S-triazine lS.1 instead of 2-bromophenanthrene Compound Q-39 (22.0 g, yield 82%; MS: [M + H] + = 704) was prepared in the same manner as in Synthesis Example 1-1 except that g, 38.1 mmol) was used.

Figure imgf000152_0002
Figure imgf000152_0002

합성예 30과 동일한 방법으로 화합물 73(9.9 gᅳ 수율 49 %; MS:[M+H]+= 705) 을 제조하였다. 합성예 33: 중간체 화합물 T-7의 제조

Figure imgf000153_0001
Compound 73 (9.9 g ᅳ yield 49%; MS: [M + H] + = 705) was prepared in the same manner as in Synthesis example 30. Synthesis Example 33 Preparation of Intermediate Compound T-7
Figure imgf000153_0001

T-1  T-1

5-클로로 2—메특시페닐보론산 ((5— chloro-2-methoxyphenyl)boronic acid)(62.2 g, 333.5 mmol) 대신 4-클로로 -2-메록시페닐보론산 ((4—chloro— 2-methoxyphenyl )boronic acid)(62.2 g, 333.5 mmol) 을 사용한 것 외에는 합성예 1의 P-1의 제조와 동일한 방법으로 화합물 T-U65.3 g, 수율 62 ； MS:[M+H]+=314) 을 제조하였다. 4-Chloro-2-methoxyphenylboronic acid ((4—chloro— 2-) instead of 5-chloro-2-methoxyphenylboronic acid ((5—chloro-2-methoxyphenyl) boronic acid) (62.2 g, 333.5 mmol) Compound T-U65.3 g, yield 62; MS: [M + H] + = 314 in the same manner as in the preparation of P-1 of Synthesis Example 1, except that methoxyphenyl) boronic acid) (62.2 g, 333.5 mmol) was used. ) Was prepared.

Figure imgf000153_0002
Figure imgf000153_0002

T-1 T-2  T-1 T-2

화합물 P-K50.0 g, 158.5匪 ol)대신 화합물 T-l(50.0 g, 158.5醒 ol) 을 사용한 것 외에는 합성예 1의 P-2의 제조와 동일한 방법으로 화합물 T- 2(43.0 g, 수율 90 %； MS:[M+H]+=300) 을 제조하였다. Compound T-2 (43.0 g, yield 90) in the same manner as in the preparation of P-2 of Synthesis Example 1, except that compound Tl (50.0 g, 158.5 μl ol) was used instead of compound P-K50.0 g, 158.5 μl) %; MS: [M + H] + = 300).

Figure imgf000153_0003
Figure imgf000153_0003

T-2 T^3  T-2 T ^ 3

화합물 P-2 (40.0 g, 132.7 醒 ol) 대신 화합물 T— 2(40.0 g, 132.7 誦 ol) 을 사용한 것 외에는 합성예 1의 P-3의 제조와 동일한 방법으로 화합물 T-3(30.6 g, 수율 82 ;MS:[M+H]+=280) 을 제조하였다. Except for using Compound T-2 (40.0 g, 132.7 誦 ol) in place of Compound P-2 (40.0 g, 132.7 醒 ol), the compound T-3 (30.6 g, Yield 82; MS: [M + H] + = 280).

Figure imgf000153_0004
Figure imgf000153_0004

Τ-3 Τ-4  Τ-3 Τ-4

화합물 P-3(30.0 g, 106.6 隱 ol) 대신 화합물 T-3(30.0 g, 106.6 誦 ol) 을 사용한 것 외에는 합성예 1의 P-4의 제조와 동일한 방법으로 화합물 T-4(25.0 g, 수율 95 ； MS:[M+H]+=247)을 제조하였다. Compound T-3 (30.0 g, 106.6 instead of Compound P-3 (30.0 g, 106.6 μL)) Except for using ol), the compound T-4 (25.0 g, yield 95; MS: [M + H] + = 247) was prepared by the same method as the preparation of P-4 of Synthesis Example 1.

Figure imgf000154_0001
Figure imgf000154_0001

T-4 T-5  T-4 T-5

화합물 P— 4(20.0 g, 81.2腿 ol) 대신 화합물 T_4(20.0 g, 81.2醒 ol) 을 사용한 것 외에는 합성예 1의 P-5의 제조와 동일한 방법으로 화합물 T- 5(31.7 g, 수율 90 %； MS:[M+H]+=434)를 제조하였다. Compound T-5 (31.7 g, Yield 90) in the same manner as in the preparation of P-5 of Synthesis Example 1 except that Compound T_4 (20.0 g, 81.2 'ol) was used instead of Compound P-4 (20.0 g, 81.2' ol). %; MS: [M + H] + = 434).

Figure imgf000154_0002
Figure imgf000154_0002

T-6  T-6

화합물 P— 4(20.0 g, 81.2匪 ol) 대신 화합물 T-4(20.0 g, 81.2 mmol), 2-ch 1 or 0-4， 6_d i pheny 1-1,3, 5-triazine 대신 2—ch 1 oro-4- (9,9-dimethyl -9H- f 1 uor en-2-y 1 ) -6-pheny 1 - 1 , 3 , 5- 1 r i az i ne ( 31.1 g, 81.2 瞧 ol) 을 사용한 것 외에는 합성예 1의 P-5의 제조와 동일한 방법으로 화합물 T-6(37.1 g, 수율 83 ； MS:[M+H]+=550)를 제조하였다. Compound P-4 (20.0 g, 81.2 μl) instead of Compound T-4 (20.0 g, 81.2 mmol), 2-ch 1 or 0-4, 6_d i pheny 1-1,3, 2—ch instead of 5-triazine 1 oro-4- (9,9-dimethyl -9H-f 1 uor en-2-y 1) -6-pheny 1-1, 3, 5- 1 ri az i ne (31.1 g, 81.2 瞧 ol) Compound T-6 (37.1 g, yield 83; MS: [M + H] + = 550) was prepared in the same manner as in the preparation of P-5 of Synthesis Example 1, except that used.

Figure imgf000155_0001
Figure imgf000155_0001

화합물 P— 4(20.0 g, 81.2 薩 ol) 대신 화합물 T-4(20.0 g, 81.2 mmol), 2-ch 1 oro-4 , 6-d i heny 1-1,3,5-triazine 대신 2-(2— chlorophenylXS- diphenyl-l,3,5-triazine(27.9 g, 81.2 mmol) 을 사용한 것 외에는 합성예 1의 p-5의 제조와 동일한 방법으로 화합물 T-7(29.4 g, 수율 71 %; MS:[M+H]+=510)를 제조하였다. Compound P-4 (20.0 g, 81.2 μl) instead of Compound T-4 (20.0 g, 81.2 mmol), 2-ch 1 oro-4, 6-di heny 1-1,3,5-triazine instead of 2- ( 2— Compound T-7 (29.4 g, yield 71%; MS) in the same manner as in the preparation of p-5 of Synthesis Example 1, except that chlorophenylXS-diphenyl-l, 3,5-triazine (27.9 g, 81.2 mmol) was used. : [M + H] + = 510).

Figure imgf000155_0002
Figure imgf000155_0002

화합물 P-6 대신 화합물 T-5C16.5 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 [1，1' :3'，1' ' :4' '，1' ' '- quaterphenyl ]-4-ylboronic acid(13.3 g, 38.1 隱 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 76(23.9 g, 수율 89 ； MS: [M+H]+= 704) 을 제조하였다. 합성예 33-2: 화합물 40의 제조 Instead of compound P-6, compound T-5C16.5 g, 38.1 mmol) and 2-bromophenanthrene instead of [1,1 ': 3' ， 1 '': 4 '' ， 1 ''' Compound 76 (23.9 g, yield 89; MS: [M + H] + = 704) was obtained in the same manner as in Synthesis Example 1-1 except that quaterphenyl] -4-ylboronic acid (13.3 g, 38.1 μl ol) was used. Prepared. Synthesis Example 33-2: Preparation of Compound 40

Figure imgf000156_0001
Figure imgf000156_0001

화합물 P-6 대신 화합물 T-6(21.0 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 (4— Instead of compound P-6 compound T-6 (21.0 g, 38.1 mmol), instead of 2-bromophenanthrene (4—

(tr iphenylsi lyl )phenyl )boronic acid(14.5 g, 38.1 画 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 40(26.6 g, 수율 82 %; MS:[M+H]+= 850) 을 제조하였다. Compound 40 (26.6 g, yield 82%; MS: [M + H] + = 850, in the same manner as in Synthesis Example 1-1 except for using (tr iphenylsi lyl) phenyl) boronic acid (14.5 g, 38.1 画 ol) ) Was prepared.

Figure imgf000156_0002
Figure imgf000156_0002

화합물 P-6 대신 화합물 T-7 19.4 g, 38.1 mmol), 2- 브로모페난트렌 (2— bromophenanthrene) 대신 f 1 uor ant hen-3-y 1 bor on i c acid(9.4 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 21(22.1 g, 수율 86 %； MS:[M+H]+= 676) 을 제조하였다. 합성예 34: 중간체 화합물 ϋ-8의 제조

Figure imgf000157_0001
19.4 g, 38.1 mmol) of compound T-7 instead of compound P-6, and f 1 uor ant hen-3-y 1 bor on ic acid (9.4 g, 38.1 mmol) instead of 2-bromophenanthrene Compound 21 (22.1 g, yield 86%; MS: [M + H] + = 676) was prepared in the same manner as in Synthesis Example 1-1 except for using. Synthesis Example 34 Preparation of Intermediate Compound X-8
Figure imgf000157_0001

1 , 3-dibromo-2-methoxybenzene( 113.2 g, 426.4 mmol)을 테트라하이드로퓨란 (1000 ml)에 녹인 후， -78°C로 온도를 낮추고 1.7 M 터셔리-부틸리튬 (t-BuLi)(251.7 ml, 426.4 mmol)을 천천히 가하였다. 동일 온도에서 한 시간 동안 교반한 후 트리아이소프로필보레이트 (B(0iPr)3)(113.2 ml, 852.4 mmol)을 가하고， 상온으로 온도를 서서히 을리면서 3시간동안 교반하였다. 반응 흔합물에 2 N 염산수용액 (800 ml)을 가하고 1.5 시간 동안 상온에서 교반하였다. 생성된 침전물을 거르고 물과 에틸에테르 (ethyl ether)로 차례로 씻은 후 진공 건조하였다. 건조 후 클로로포름과 에틸아세테이트로 재결정하고 건조하여 (3_bromo— 2— methoxyphenyl )boronic acid(89.6 g, 수율 91 %； MS:[M+H]+=230)을 제조하였다. Dissolve 1, 3-dibromo-2-methoxybenzene (113.2 g, 426.4 mmol) in tetrahydrofuran (1000 ml), lower the temperature to -78 ° C, and 1.7 M tert-butyllithium (t-BuLi) (251.7 ml, 426.4 mmol) was added slowly. After stirring at the same temperature for 1 hour, triisopropylborate (B (0iPr) 3 ) (113.2 ml, 852.4 mmol) was added thereto, and the mixture was stirred for 3 hours while slowly cooling to room temperature. 2 N aqueous hydrochloric acid solution (800 ml) was added to the reaction mixture, which was stirred for 1.5 hours at room temperature. The resulting precipitate was filtered off, washed sequentially with water and ethyl ether, and dried in vacuo. After drying, the mixture was recrystallized with chloroform and ethyl acetate and dried to prepare (3_bromo— 2—methoxyphenyl) boronic acid (89.6 g, yield 91%; MS: [M + H] + = 230).

Figure imgf000157_0002
Figure imgf000157_0002

U-1  U-1

브로모 -3-플루오로 -2-요오드벤젠 ( l-bromo-3-f 1 uoro-2- i odobenzene ) 대신 1-클로로-3-플루'오로-2-요오드벤젠(1-(±101"으3에1101"0-2- i odobenzene )(85.5 g, 333.5 mmol), 5-클로로 -2—메특시페닐보론산 ((5- chloro-2-methoxyphenyl )boronic acid) 대신 3一브로모— 2— 메특시페닐보론산 (3-bromo— 2-methoxyphenyl)boronic acid) (77.0 g, 333.5 mmol) 을 사용한 것 외에는 합성예 1의 P-1의 제조와 동일한 방법으로 화합물 U-K55.8 g, 수율 53 %； MS:[M+H]+=314) 을제조하였다. L-bromo-3-f 1 uoro-2- i odobenzene instead of 1-chloro-3-flu'or-2-iodinebenzene (1- (± 101 " 1110 "0-2- i odobenzene) (85.5 g, 333.5 mmol), 5-chloro-2-2-methoxyphenylboronic acid ((5-chloro-2-methoxyphenyl) boronic acid) 2— Compound U-K55.8 g in the same manner as in the preparation of P-1 of Synthesis Example 1, except that 3-bromo- 2-methoxyphenyl) boronic acid (77.0 g, 333.5 mmol) was used. , Yield 53%; MS: [M + H] + = 314) was prepared.

Figure imgf000157_0003
화합물 P-K50.0 g, 158.5隱 ol)대신 화합물 U-l( 50.0 g, 158.5 mmol) 을 사용한 것 외에는 합성예 1의 P-2의 제조와 동일한 방법으로 화합물 U- 2(39.7 g, 수율 83 %; MS:[M+H]+=300) 을 제조하였다.
Figure imgf000157_0003
Compound U-2 (39.7 g, Yield 83%) in the same manner as in the preparation of P-2 of Synthesis Example 1, except that Compound Ul (50.0 g, 158.5 mmol) was used instead of Compound P-K50.0 g, 158.5 μL) MS: [M + H] + = 300).

Figure imgf000158_0001
Figure imgf000158_0001

화합물 P-2(40.0 g, 132.7 匪 ol) 대신 화합물 U_2(40.0 g, 132.7 隱 ol) 을 사용한 것 외에는 합성예 1의 P-3의 제조와 동일한 방법으로 화합물 U-3(31.4 g, 수율 84 %;MS:[M+H]+=280) 을 제조하였다. Compound U-3 (31.4 g, Yield 84) in the same manner as in the preparation of P-3 of Synthesis Example 1, except that compound U_2 (40.0 g, 132.7 隱 ol) was used instead of compound P-2 (40.0 g, 132.7 匪 ol). %; MS: [M + H] + = 280).

Figure imgf000158_0002
Figure imgf000158_0002

화합물 P-3(30.0 g, 106.6 瞧 ol) 대신 화합물 U-3(30.0 g, 106.6 隱 ol) 을 사용한 것 외에는 합성예 1의 P-4의 제조와 동일한 방법으로 화합물 U-4(25.5 g, 수율 97 %； MS:[M+H]+=247)을 제조하였다. Compound U-4 (25.5 g, 25.5 g, 106.6 μl ol) instead of compound U-3 (30.0 g, 106.6 μl ol) was used in the same manner as in Preparation of P-4 of Synthesis Example 1 Yield 97%; MS: [M + H] + = 247).

Figure imgf000158_0003
Figure imgf000158_0003

화합물 P-4(20.0 g, 81.2隱 ol) 대신 화합물 U-4(20.0 g, 81.2醒 ol) 2-ch 1 oro-4， 6— d i pheny 1-1,3, 5-triazine 대신 tri pheny 1 en-2-y 1 boron i c acid(22.1 g, 81.2 瞧 ol) 을 사용한 것 외에는 합성예 1의 P-5의 제조와 동일한 방법으로 화합물 U-5(31.1 g, 수율 86 %; MS:[M+H]+=445)를 제조하였다. Compound U-4 (20.0 g, 81.2 醒 ol) instead of compound P-4 (20.0 g, 81.2y ol) 2-ch 1 oro-4 ， 6— di pheny 1-1,3, tri pheny 1 instead of 5-triazine Except for using en-2-y 1 boron ic acid (22.1 g, 81.2 瞧 ol), the compound U-5 (31.1 g, yield 86%; MS: [M + H] + = 445).

Figure imgf000159_0001
Figure imgf000159_0001

화합물 Q_5(25.0 g, 52.8 聽 ol) 대신 화합물 Ih5(22.6 g, 52.8 mmol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 U-6(24.7 g, 수율 90 %； MS:[M+H]+= 521) 을 제조하였다. Compound U-6 (24.7 g, Yield 90%; MS: [M +] in the same manner as in Synthesis Example 4-2 except for using the compound Ih5 (22.6 g, 52.8 mmol) instead of the compound Q_5 (25.0 g, 52.8 μL). H] + = 521).

Figure imgf000159_0002
Figure imgf000159_0002

화합물 P-4 대신 화합물 U-4(20.0 g, 81.2 mmol), 2-chloro— 4，6_ diphenyl-l,3,5-tr iazine 대신 [1,1'：4' ,1' '-terphenyl]-4-ylboronic acid(22.3 g, 81.2 瞧 ol) 을 사용한 것 외에는 합성예 1의 P-5의 제조와 동일한 방법으로 화합물 U-7(30.8 g, 수율 88 %; MS:[M+H]+=431)를 제조하였다. Instead of compound P-4 compound U-4 (20.0 g, 81.2 mmol), 2-chloro-4,6_diphenyl-l, 3,5-tr iazine [1,1 '： 4', 1 '' -terphenyl] Compound U-7 (30.8 g, yield 88%; MS: [M + H] + in the same manner as in the preparation of P-5 of Synthesis Example 1, except that 4-ylboronic acid (22.3 g, 81.2 瞧 ol) was used = 431).

Figure imgf000159_0003
Figure imgf000159_0003

화합물 Q-5 대신 화합물 U-7(22.8 g, 52.8隱 ol)을 사용한 것 외에 합성예 4-2와 동일한 방법으로 화합물 U-8(24.3 g, 수율 88 %； MS:[M+H] 523) 을 제조하였다. 합성예 34-1: 화합물 22의 제조 Compound U-8 (24.3 g, Yield 88%; MS: [M + H] 523) in the same manner as in Synthesis Example 4-2, except that Compound U-7 (22.8 g, 52.8 隱 ol) was used instead of Compound Q-5. ) Was prepared. Synthesis Example 34-1: Preparation of Compound 22

Figure imgf000160_0001
Figure imgf000160_0001

화합물 P-6 대신 화합물 U-6 19.8 g, 38.1 mmol), 2- 브로모페난트렌 (2-br이 nophenanthrene) 대신 2-( [1， Γ— biphenyl ]-4-yl )-4- chloro-6-phenyl-l,3,5-triazine(13.1 g, 38.1 瞧 ol)을 사용한 것 외에는 합성예 1—1과 동일한 방법으로 화합물 22(35.4 g, 수율 93 %； MS:[M+H]+= 702) 을 제조하였다. Instead of compound P-6, compound U-6 19.8 g, 38.1 mmol), 2-bromophenanthrene (2-br nophenanthrene) instead of 2- ([1, Γ— biphenyl] -4-yl) -4-chloro- Compound 22 (35.4 g, yield 93%; MS: [M + H] + in the same manner as in Synthesis Example 1-1 except that 6-phenyl-l, 3,5-triazine (13.1 g, 38.1 瞧 ol) was used = 702).

Figure imgf000160_0002
Figure imgf000160_0002

화합물 P-6 대신 화합물 U— 8(19.9 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-chloro-4- Compound U-8 instead of compound P-6 (19.9 g, 38.1 mmol), 2-chloro-4- instead of 2-bromophenanthrene

( d i benzo [ b , d] f ur an-2-y 1 ) -6-pheny 1 - 1 , 3 , 5- 1 r i az i ne ( 13.6 g, 38.1 圆 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 77(24.9 g, 수율 91 %; MS:[M+H]+= 718) 을 제조하였다. 합성예 35: 중간체 화합물 W-8의 제조

Figure imgf000161_0001
Synthesis Example 1- except that (di benzo [b, d] f ur an-2-y 1) -6-pheny 1-1, 3, 5- 1 ri az i ne (13.6 g, 38.1 圆 ol) was used. Compound 77 (24.9 g, yield 91%; MS: [M + H] + = 718) was prepared in the same manner as 1. Synthesis Example 35 Preparation of Intermediate Compound W-8
Figure imgf000161_0001

2-br omo- 1 , 3~d i met hoxybenzene (92.6 g, 426.4 mmol)을 테트라하이드로퓨란 (1000 ml)에 녹인 후， -78°C로 은도를 낮추고 1.7 M 터셔리-부틸리튬 (t-BuLi)(251.7 ml, 426.4 mmol)을 천천히 가하였다. 동일 온도에서 한 시간 동안 교반한 후 트리아이소프로필보레이트 (B(0iPr)3)(113.2 ml, 852.4 匪 ol)을 가하고， 상온ᅳ으로 온도를 서서히 을리면서 3시간동안 교반하였다. 반응 흔합물에 2 N 염산수용액 (800 ml)을 가하고 1.5 시간 동안 상온에서 교반하였다. 생성된 침전물을 거르고 물과 에틸에테르 (ethyl ether)로 차례로 씻은 후 진공 건조하였다. 건조 후 클로로포름과 에틸아세테이트로 재결정하고 건조하여 (2,6-dimethoxyphenyl)boronic acid(63.6 g, 수율 82 ； MS: [M+H]+=183)을 제조하였다. Dissolve 2-br omo- 1, 3 ~ di methoxybenzene (92.6 g, 426.4 mmol) in tetrahydrofuran (1000 ml), lower the silver to -78 ° C and 1.7 M tert-butyllithium (t-BuLi ) (251.7 ml, 426.4 mmol) was added slowly. After stirring for 1 hour at the same temperature, triisopropylborate (B (0iPr) 3 ) (113.2 ml, 852.4 匪 ol) was added and stirred for 3 hours while slowly cooling the temperature to room temperature ᅳ. 2 N aqueous hydrochloric acid solution (800 ml) was added to the reaction mixture, which was stirred for 1.5 hours at room temperature. The resulting precipitate was filtered off, washed sequentially with water and ethyl ether, and dried in vacuo. After drying, recrystallized with chloroform and ethyl acetate and dried to prepare (2,6-dimethoxyphenyl) boronic acid (63.6 g, yield 82; MS: [M + H] + = 183).

Figure imgf000161_0002
브로모 -3-플루오로 -2-요오드벤젠 ( l-bromo-3- f 1 uoro-2- i odobenzene ) 대신 1-클로로 -3-플루오로 -2-요오드벤젠 (l-chloro-3-fluoro— 2— iodobenzene)(85.5 g, 333.5 mmol), 5-클로로 -2-메록시페닐보론산 ((5- ch 1 oro-2-me t hoxypheny Dboronic acid) 대신 (2，6— dimet hoxypheny 1 ) bor on i c acid(60.7 g, 333.5 mmol) 을 사용한 것 외에는 합성예 1의 P-1의 제조와 동일한 방법으로 화합물 W- 35.6 g, 수율 40 % MS: [M+H]+=267) 을 제조하였다.
Figure imgf000162_0001
Figure imgf000161_0002
1-chloro-3-fluoro-2-iodinebenzene (l-chloro-3-fluoro instead of l-bromo-3-f 1 uoro-2-iodobenzene) — 2— iodobenzene) (85.5 g, 333.5 mmol), instead of 5-chloro-2-methoxyphenylboronic acid ((5- ch 1 oro-2-me t hoxypheny Dboronic acid) (2，6— dimet hoxypheny 1) Compound W-35.6 g, yield 40% MS: [M + H] + = 267) was obtained by the same method as the preparation of P-1 of Synthesis Example 1, except that bor on ic acid (60.7 g, 333.5 mmol) was used. It was.
Figure imgf000162_0001

화합물 P-K50.0 g, 158.5 mmol)대신 화합물 W-l(42.3 g, 158.5 ■ol), 보론트리브로마이드 (boron tr ibromide)(31.6 ml , 332.9 mmol) 을 사용한 것 외에는 합성예 1의 P-2의 제조와 동일한 방법으로 화합물 W- 2(33.3 g, 수율 88 %； MS:[M+H]+=239) 을 제조하였다. P-2 of Synthesis Example 1 except that Compound Wl (42.3 g, 158.5 mmol) and boron tribromide (31.6 ml, 332.9 mmol) were used instead of Compound P-K50.0 g, 158.5 mmol). Compound W-2 (33.3 g, yield 88%; MS: [M + H] + = 239) was prepared in the same manner as in the preparation.

Figure imgf000162_0002
Figure imgf000162_0002

W-2 W-3  W-2 W-3

화합물 P-2(40.0 g, 132.7 圆 ol) 대신 화합물 W— 2(31.7 g, 132.7 mmol) 을 사용한 것 외에는 합성예 1의 P-3의 제조와 동일한 방법으로 화합물 W-3(23.5 g, 수율 81 %;MS:

Figure imgf000162_0003
을 제조하였다. Compound W-3 (23.5 g, yield) in the same manner as in the preparation of P-3 of Synthesis Example 1 except that Compound W-2 (31.7 g, 132.7 mmol) was used instead of Compound P-2 (40.0 g, 132.7 圆 ol) 81%; MS:
Figure imgf000162_0003
Was prepared.

Figure imgf000162_0004
Figure imgf000162_0004

W-3 W-4  W-3 W-4

화합물 W-3 (20.0 g, 91.5 mmol)을 아세토나이트릴 (250 ml)에 분산 시킨뒤 칼슘카보네이트 (51.2 g, 109.8 mmol)와 Nonaf luorobutanesulfonyl fluoride(41.6 g, 137.3 隱 ol)을 넣었다. 위 흔합물을 80°C에서 1시간 동안 교반하였다. 반웅물을 상온으로 식힌 뒤 필터하여 에탄을과 물로 씻어준뒤 건조하여 화합물 W-4(38.9 g' 수율 85 %； MS:[M+H]+=500)을 얻었다. Compound W-3 (20.0 g, 91.5 mmol) was dispersed in acetonitrile (250 ml), and calcium carbonate (51.2 g, 109.8 mmol) and Nonaf luorobutanesulfonyl fluoride (41.6 g, 137.3 隱 ol) were added thereto. The gastric mixture was stirred at 80 ° C for 1 hour. The reaction product was cooled to room temperature, filtered, washed with ethane and water, and dried to obtain compound W-4 (38.9 g 'yield 85%; MS: [M + H] + = 500).

Figure imgf000163_0001
화합물 P-4 대신 화합물 W-4(40.7 g, 81.2 醒 ol), 2-chloro-4,6- di pheny 1-1, 3, 5-tr iazine 대신 t r i pheny 1 en-2-y 1 bor on i c acid(22.1 g, 81.2 mmol) 을 사용한 것 외에는 합성예 1의 P-5의 제조와 동일한 방법으로 화합물 W-5(21.6 g, 수율 62 %; MS:[M+H]+=429)를 제조하였다.
Figure imgf000163_0001
Compound W-4 instead of compound P-4 (40.7 g, 81.2 P ol), tri pheny 1 en-2-y 1 bor on instead of 2-chloro-4,6- di pheny 1-1, 3, 5-tr iazine Compound W-5 (21.6 g, yield 62%; MS: [M + H] + = 429) was obtained in the same manner as in the preparation of P-5 of Synthesis Example 1, except that ic acid (22.1 g, 81.2 mmol) was used. Prepared.

Figure imgf000163_0002
Figure imgf000163_0002

화합물 Q-5 대신 화합물 W-5(22.6 g, 52.8圆 ol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 W-6(23.4 g, 수율 85 %； MS:[M+H]+= 521) 을 제조하였다. Compound W-6 (23.4 g, Yield 85%; MS: [M + H] + ) in the same manner as in Synthesis Example 4-2, except that Compound W-5 (22.6 g, 52.8 圆 ol) was used instead of Compound Q-5. 521).

Figure imgf000164_0001
Figure imgf000164_0001

화합물 P-4 대신 화합물 W— 4(40.7 g, 81.2 腿 ol), 2-chloro-4,6- diphenyl-1,3, 5-triazine 대신 [1,1'：4' ,1' ' -terphenyl ]-3-ylboronic acid(22.3 g, 81.2 mmol) 을 사용한 것 외에는 합성예 1의 P—5의 제조와 동일한 방법으로 화합물 W-7(22.0 g, 수율 63 .%; MS:[M+H]+=431)를 제조하였다. Compound W-4 instead of compound P-4 (40.7 g, 81.2 μl ol), instead of 2-chloro-4,6-diphenyl-1,3,5-triazine [1,1 '： 4', 1 '' -terphenyl ] -3-ylboronic acid (22.3 g, 81.2 mmol) except that the compound W-7 (22.0 g, yield 63.%; MS: [M + H] was obtained by the same method as the preparation of P-5 in Synthesis Example 1. + = 431).

Figure imgf000164_0002
Figure imgf000164_0002

합성예 4-2와 동일한 방법으로 화합물 W-8(22.1 g, 수율 80 %； MS:[M+H]+= 523) 을 제조하였다. 합성예 35-1: 화합물 16의 제조 Compound W-8 (22.1 g, yield 80%; MS: [M + H] + = 523) was prepared in the same manner as in Synthesis example 4-2. Synthesis Example 35-1: Preparation of Compound 16

Figure imgf000165_0001
Figure imgf000165_0001

화합물 p-6 대신 화합물 W-6(19.8 g, 38.1 腿 ol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-(4-chlorophenyl)_4,6- diphenyl-l,3,5-triazine(13.1 g, 38.1 隱 ol)을 사용한 것 외에는 합성예 Compound W-6 (19.8 g, 38.1 腿 ol) instead of p-6, 2- (4-chlorophenyl) _4,6-diphenyl-l, 3,5-triazine instead of 2-bromophenanthrene Synthesis example except for using (13.1 g, 38.1 隱 ol)

1-1과 동일한 방법으로 화합물 16(19.5 g, 수율 73 ； MS: [M+H]+= 702) 을 제조하였다. Compound 16 (19.5 g, yield 73; MS: [M + H] + = 702) was prepared in the same manner as in 1-1.

화합물 P— 6 대신 화합물 W-8 19.9 g, 38.1 mmol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-chloro-4,6_diphenyl-l,3,5- triazine(10.2 g, 38.1 匪 ol)을 사용한 것 외에는 합성예 1—1과 동일한 방법으로 화합물 37(15.5 g, 수율 65 %; MS:[M+H]+ = 628) 을 제조하였다. 19.9 g, 38.1 mmol) instead of compound P-6, 2-chloro-4,6_diphenyl-l, 3,5-triazine (10.2 g, 38.1 匪 ol) instead of 2-bromophenanthrene ) Compound 37 (15.5 g, yield 65%; MS: [M + H] + = 628) was prepared in the same manner as in Synthesis Example 1-1 except that was used.

Figure imgf000165_0003
2-클로로디밴조티오펜 50g(23.0 mmol)올 클로로포름 300mL 에 희석한 후 브로민 18mL(0.34mol)를 서서히 투입하여 실은에서 12시간 교반시켰다. 반웅이 종결된 후 석출된 고체를 여과하고， 이를 다시 과량의 클로로포름에 가온하여 녹인 후 20%의 소듐티오설페이트 수용액으로 세척하여 유기층을 분리하였다. 이를 다시 탄산수소나트륨 포화 수용액으로 세척하여 유기층을 분리하고, 무수황산마그네슴으로 수분을 건조하여 감압 농축하였다. 농축한 화합물에 에틸아세테이트 300mL을 넣고 환류 교반하여 슬러리하고 이를 실온으로 식혀서 여과하였다. 질소하에 건조하여 연한 갈색의 화합물 X- 1을 (32 g, 수율 47%; MS:[M+H]+ = 296) 을 제조하였다.
Figure imgf000165_0003
After diluting 50 g (23.0 mmol) of 2-chlorodivanzothiophene in 300 mL of chloroform, 18 mL (0.34 mol) of bromine was slowly added thereto, followed by stirring at room temperature for 12 hours. After the reaction was finished, the precipitated solid was filtered, dissolved in warm chloroform, and then washed with 20% aqueous sodium thiosulfate solution to separate the organic layer. The organic layer was washed again with a saturated aqueous solution of sodium bicarbonate, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. 300 mL of ethyl acetate was added to the concentrated compound, and the mixture was stirred at reflux to slurry, which was cooled to room temperature and filtered. Drying under nitrogen gave light brown compound X-1 (32 g, yield 47%; MS: [M + H] + = 296).

Figure imgf000166_0001
Figure imgf000166_0001

화합물 X-1 48 g(0.16mol)을 1，4-다이옥산 500mL에 녹인 후 Bis(pinacolato)diboron 49 g(0.19mol)을 투입하였다. 흔합물을 교반 하면서 포타슘아세테이트 31.4 g(0.32mol)를 첨가하고 가온 하여 환류 시켰다. 환류 교반 상태에서 디벤질리덴아세톤팔라듐 2.7 g(0.005mol) 과 트리시클로핵실포스핀 2.7 g(O.Olmol)을 첨가하고 12시간 환류 교반시켰다. 반웅 종결 후 반웅물을 실온으로 냉각하여 물로 세척 후 클로로포름으로 2회 추출하였다. 모아진 유기층을 다시 한번 물로 세척 후 무수황산마그네슘으로 수분을 제거하고 여과하여 농축하였다. 농축한 물질을 소량의 에틸아세테이트와 과량의 핵산 흔합용액으로 가열 교반 하고 여과하여 흰색의 화합물 X-2를 (43 gᅳ 수율 78%; MS:[M+H]+ = 345) 을 제조하였다. 48 g (0.16 mol) of Compound X-1 was dissolved in 500 mL of 1,4-dioxane, and 49 g (0.19 mol) of Bis (pinacolato) diboron was added thereto. While stirring the mixture, 31.4 g (0.32 mol) of potassium acetate was added thereto, and the mixture was heated to reflux. 2.7 g (0.005 mol) of dibenzylidene acetone palladium and 2.7 g (O.mol) of tricyclonucleosilphosphine were added under reflux stirring, and the mixture was stirred under reflux for 12 hours. After completion of reaction, the reaction product was cooled to room temperature, washed with water, and extracted twice with chloroform. The combined organic layers were washed with water once more, and then dried with anhydrous magnesium sulfate, filtered and concentrated. The concentrated material was heated and stirred with a small amount of ethyl acetate and an excess nucleic acid mixture solution and filtered to give white Compound X-2 (43 g43 yield 78%; MS: [M + H] + = 345).

Figure imgf000167_0001
Figure imgf000167_0001

화합물 X-2 10g(0.03mol)과 2-chloro-4,6-diphenyl-l,3,5-triazine 8.4 g(0.03mol)을 1,4-dioxane 100 mL에투입하여 녹인 후 K3P04 19g(0.09mol)을 투입하여 환류 상태에서 교반 시켰다. 이 흔합물에 디벤질리덴아세톤팔라듐 570mg(0.001mol) 과 트리시클로핵실포스핀 560mg(0.002mol)을 첨가하고 12시간 환류 교반시켰다. 반웅 종결 후 반응물을 실온으로 냉각하여 물로 세척하고 에틸아세테이트로 2회 추출하여 무수황산마그네슘으로 수분을 제거하고 여과하여 소량의 에틸아세테이트가 남도록 감압 농축하였다. 농축한 화합물에 아세톤을 과량 투입하여 슬러리 후 여과하여 흰색의 화합물 X-3을 (11 g, 수율 83%; MS:[M+H]+ = 150) 을 제조하였다. 10 g (0.03 mol) of compound X-2 and 8.4 g (0.03 mol) of 2-chloro-4,6-diphenyl-l, 3,5-triazine were added and dissolved in 100 mL of 1,4-dioxane, followed by 19 g (0.09 K3P04). mol) was added and stirred under reflux. To this mixture was added 570 mg (0.001 mol) of dibenzylidene acetone palladium and 560 mg (0.002 mol) of tricyclonucleosilphosphine, followed by stirring under reflux for 12 hours. After completion of reaction, the reaction mixture was cooled to room temperature, washed with water, extracted twice with ethyl acetate, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to leave a small amount of ethyl acetate. Acetone was added to the concentrated compound in an excess amount, and the slurry was filtered and then filtered to obtain white Compound X-3 (11 g, yield 83%; MS: [M + H] + = 150).

Figure imgf000167_0002
Figure imgf000167_0002

10g(0.022mol )과 t r i pheny 1 en-2-y 1 bor on i c acid 6.0g(0.022mol)을 1,4-dioxane 80mL에 희석하고 K3P04 13.9g(0.066mol))을 흔합용액에 투입 후 가온하여 환류 상태에서 교반시켰다. 이 흔합물에 디벤질리덴아세  Dilute 10 g (0.022 mol) and 6.0 g (0.022 mol) of tri pheny 1 en-2-y 1 bor on ic acid in 80 mL of 1,4-dioxane and add 13.9 g (0.066 mol) of K3P04 to the mixture The mixture was stirred at reflux. Dibenzylidene acetic acid in this mixture

톤팔라듐 3801 (0.66隱01)과 트리시클로핵실포스핀 370mg(1.3mmol)을 첨가하고 12시간 환류 교반시켰다. 반웅 종결 후 반웅물을 실온으로 넁각하여 석출된 고체를 여과하고， 이를 클로로포름에 녹인 후 물로 2회 세척하고 모아진 유기층을 무수황산마그네슘으로 수분을 제거하고 여과하여 클로로포름과 에틸아세테이트를 흔합액으로 사용하여 재결정하는 방법으로 정제하여 흰색의 화합물 A를 (9.6 g, 수율 68%; MS:[M+H]+ = 642) 을 제조하였다. Tonpalladium 3801 (0.66 × 10 1) and 370 mg (1.3 mmol) of tricyclonucleosilphosphine were added and stirred under reflux for 12 hours. After completion of reaction, the reaction product was cooled to room temperature, and the precipitated solid was filtered. The precipitated solid was dissolved in chloroform and washed twice with water. By recrystallization Purification gave white Compound A (9.6 g, yield 68%; MS: [M + H] + = 642).

Figure imgf000168_0001
화합물 P-4 대신 화합물 Q-3(20.1 g, 81.2 mmol), 2-chloro-4,6- diphenyl-1 ,3,5-tr iazine 대신 (4_(4,6-diphenylᅳ l,3,5-triazin-2_ yl)phenyl)boronic acid(28.7 g, 81.2 mmol) 을 사용한 것 외에는 합성예 1의 P-5의 제조와 동일한 방법으로 화합물 B(35.5 g, 수율 92 %； MS:[M+H]+=476)를 제조하였다.
Figure imgf000168_0001
Instead of compound P-4 Compound Q-3 (20.1 g, 81.2 mmol), instead of 2-chloro-4,6-diphenyl-1, 3,5-tr iazine (4_ (4,6-diphenyl ᅳ l, 3,5 Except for using -triazin-2_yl) phenyl) boronic acid (28.7 g, 81.2 mmol), Compound B (35.5 g, Yield 92%; MS: [M + H; ] + = 476).

Figure imgf000168_0002
Figure imgf000168_0002

4,6-Dibromodibenzofuran(20 g, 61.4 mmol) , [1,1'：4' ,1' '- terphenyl]ᅳ 3ᅳ ylboronic acid(17.6 g, 61.4 隱 ol)을 테트라하이드로퓨란 (400 ml)에 분산시킨 후， 2M 탄산칼륨수용액 (aq. K2C03)(92.1 ml, 184.2 隱 ol)을 첨가하고 테트라키스트리페닐포스피노팔라듐 [Pd(PPh3)4](1.4 g, 2 mol¾ 을 넣은 후 3시간 동안 교반 환류하였다. 상은으로 온도를 낮추고 생성된 흔합물을 물과 를루엔으로 추출한 뒤 유기층을 황산마그네슘 (MgS04)로 건조한 뒤 감압증류 하였다. 얻어진 흔합물을 컬럼크로마토그피로 실리카겔에서 핵산:에틸아세테이트 (15:1)로 정제하여 화합물 X-4(54.3 g, 수율 62 %； MS:[M+H]+=475)를 제조하였다. 4,6-Dibromodibenzofuran (20 g, 61.4 mmol), [1,1 '： 4', 1 ''-terphenyl] '3'ylboronic acid (17.6 g, 61.4 隱 ol) was added to tetrahydrofuran (400 ml). After dispersion, 2M aqueous potassium carbonate solution (aq. K 2 C0 3 ) (92.1 ml, 184.2 2 ol) was added and tetrakistriphenylphosphinopalladium [Pd (PPh 3 ) 4 ] (1.4 g, 2 mol¾) was added thereto. The mixture was cooled to reflux for 3 hours, and the resulting mixture was extracted with water and toluene, and then the organic layer was dried over magnesium sulfate (MgS0 4 ) and distilled under reduced pressure. Purification with nucleic acid: ethyl acetate (15: 1) gave compound X-4 (54.3 g, yield 62%; MS: [M + H] + = 475).

Figure imgf000169_0001
Figure imgf000169_0001

화합물 Q-5(25.0 g, 52.8 腿 ol) 대신 화합물 X-4(25.1 g, 52.8 mmol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 Χ-5(25·4 g, 수율 92 %； MS:[M+H]+= 523) 을 제조하였다. Compound C-5 (25 · 4 g, yield 92%) in the same manner as in Synthesis Example 4-2 except for using Compound X-4 (25.1 g, 52.8 mmol) instead of Compound Q-5 (25.0 g, 52.8 μL) MS: [M + H] + = 523).

Figure imgf000169_0002
Figure imgf000169_0002

화합물 P-6 대신 화합물 X-5(19.9 g, 38.1 隱 ol), 2- 브로모페난트렌 (2-bromophenanthrene) 대신 2-chloro-4,6-diphenyl-l,3,5- triazine(10.2 g, 38.1 mmol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 CC19.9 g, 수율 83 %; MS:[M+H]+= 628) 을 제조하였다. 합성예 39: 화합물 D의 제조

Figure imgf000169_0003
Compound X-5 (19.9 g, 38.1 隱 ol) instead of P-6, 2-chloro-4,6-diphenyl-l, 3,5- triazine (10.2 g) instead of 2-bromophenanthrene , 38.1 mmol) except that the compound CC19.9 g, yield 83%; MS: [M + H] + = 628). Synthesis Example 39 Preparation of Compound D
Figure imgf000169_0003

화합물 P-3 대신 4-br omod i benzo [ b , d ] f ur an ( 26.3 g, 106.6 mmol) 을 사용한 것 외에는 합성예 1의 P-4의 제조와 동일한 방법으로 dibenzo[b,d]furan-4-ylboronic acid(21.2 g, 수율 94 %; MS:[M+H]+= 213)을 제조하였다. Dibenzo [b, d] furan was prepared in the same manner as in the preparation of P-4 of Synthesis Example 1, except that 4-br omod i benzo [b, d] f ur an (26.3 g, 106.6 mmol) was used instead of compound P-3. 4-ylboronic acid (21.2 g, yield 94%; MS: [M + H] + = 213) was prepared.

Figure imgf000169_0004
화합물 P-4 대신 4-bromodibenzo[b , d] thi ophene(21.4 g, 81.2 mmol), 2-ch 1 or 0-4 , 6-d i phenyl -1 , 3 , 5-t r i az i ne 대신 dibenzo[b,d] furan-4- ylboronic acid(17.2 g, 81.2 mmol) 을 사용한 것 외에는 합성예 1의 P-5의 제조와 동일한 방법으로 화합물 X-6(25.3 g, 수율 89 ； MS:[M+H]+=351)를 제조하였다.
Figure imgf000169_0004
4-bromodibenzo [b, d] thi ophene (21.4 g, 81.2 mmol) instead of compound P-4, 2-ch 1 or 0-4, dibenzo [instead of 6-di phenyl -1, 3, 5-tri az i ne b, d] Compound X-6 (25.3 g, yield 89; MS: [M +] in the same manner as in the preparation of P-5 of Synthesis Example 1, except that furan-4-ylboronic acid (17.2 g, 81.2 mmol) was used. H] + = 351).

Figure imgf000170_0001
Figure imgf000170_0001

화합물 R-4 대신 화합물 X-6(25.0 g, 71.3 mmol), 클로로포름 (200 ml), 아세트산 (200 ml), Br2(3.8 mL, 74.9 隨 ol)을 사용한 것 외에는 합성예 20 의 화합물 R-5의 제조법과 동일한 방법으로 얻은 흔합물을 컬럼크로마토그래피로 실리카겔에서 핵산:에틸아세테이트 (10:1)로 정제하여 화합물 Χ-7(14·4 g, 수율 47 %； MS:[M+H]+= 428) 을 제조하였다. Compound R- of Synthesis Example 20 except for using compound X-6 (25.0 g, 71.3 mmol), chloroform (200 ml), acetic acid (200 ml), Br 2 (3.8 mL, 74.9 μl) instead of compound R-4 The mixture obtained in the same manner as in the preparation of 5 was purified by column chromatography on silica gel with nucleic acid: ethyl acetate (10: 1) to obtain the compound Χ-7 (14 · 4 g, yield 47%; MS: [M + H] + = 428).

Figure imgf000170_0002
Figure imgf000170_0002

화합물 Q-5 대신 화합물 X-7(22.7 g, 52.8 mmol)을 사용한 것 외에는 합성예 4-2와 동일한 방법으로 화합물 X-8(23.9 g, 수율 95 %； MS:[M+H]+= 477) 을 제조하였다. Compound X-8 (23.9 g, yield 95%; MS: [M + H] + = in the same manner as in Synthesis Example 4-2 except for using compound X-7 (22.7 g, 52.8 mmol) instead of compound Q-5 477) was prepared.

Figure imgf000171_0001
Figure imgf000171_0001

화합물 P-6 대신 화합물 X-8(18.2 g' 38.1 mmol), 2- 브로모페난트렌 (2-broiTK)phenan1:hrene) 대신 2—chloro—4,6-diphenyl-l,3,5- triazine(10.2 g, 38.1 mmol)올 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 D 19.7 g, 수율 89 %； MS:[M+H]+= 582) 을 제조하였다. 2—chloro—4,6-diphenyl-l, 3,5-triazine instead of compound X-8 (18.2 g '38.1 mmol) and 2-bromophenanthrene (2-broiTK) phenan1: hrene) instead of compound P-6 Compound D 19.7 g, yield 89%; MS: [M + H] + = 582) was prepared in the same manner as in Synthesis Example 1-1 except for using (10.2 g, 38.1 mmol) ol.

Figure imgf000171_0002
Figure imgf000171_0002

2-클로로디벤조티오펜 대신 2-클로로디벤조퓨란 (46.6 g, 230.0 mmol)을 사용한 것 외에는 합성예 36 의 X-1의 제조법과 동일한 방법으로 화합물 X-9(56.3 g, 수율 87 %； MS:[M+H]+= 280) 을 제조하였다. Compound X-9 (56.3 g, yield 87%) in the same manner as in the preparation of X-1 of Synthesis Example 36, except that 2-chlorodibenzofuran (46.6 g, 230.0 mmol) was used instead of 2-chlorodibenzothiophene; MS: [M + H] + = 280).

Figure imgf000171_0003
Figure imgf000171_0003

화합물 P-4 대신 화합물 X-9(22.9 g, 81.2 mmol), 2-chloro-4,6- diphenylᅳ 1，3，5ᅳ triazine 대신 phenyl boron ic acid(17.3 g, 81.2 mmol ) 을 사용한 것 외에는 합성예 1의 P-5의 제조와 동일한 방법으로 화합물 Xᅳ 10(21.7 g, 수율 96 %； MS:[M+H]+=279)를 제조하였다. Except for using compound X-9 (22.9 g, 81.2 mmol) and 2-chloro-4,6-diphenyl ᅳ 1,3,5 ᅳ triazine instead of compound P-4, except phenyl boron ic acid (17.3 g, 81.2 mmol) was used. Compound X # 10 (21.7 g, yield 96%; MS: [M + H] + = 279) was prepared in the same manner as in the preparation of P-5 of Synthesis Example 1.

Figure imgf000172_0001
Figure imgf000172_0001

화합물 P-6 대신 화합물 X-10(10.6 g, 38.1 匪 ol), 2- 브로모페난트렌 (2— bromophenanthrene) 대신 t r i pheny 1 en-2-y 1 boron i c acid(10.4 g, 38.1 誦 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 E(15.6 g, 수율 87 %; MS:[M+H]+= 471) 을 제조하였다. Instead of compound P-6 compound X-10 (10.6 g, 38.1 匪 ol), 2-bromophenanthrene (2—bromophenanthrene) tri pheny 1 en-2-y 1 boron ic acid (10.4 g, 38.1 誦 ol) Compound E (15.6 g, yield 87%; MS: [M + H] + = 471) was prepared in the same manner as in Synthesis Example 1-1 except for using.

Figure imgf000172_0002
Figure imgf000172_0002

X-11  X-11

화합물 P-4 대신 di benzo [b , d] f uran-4-yl boron i c acid(17.2 g, 81.2 瞧 ol), 2-chloro-4,6-di henyl-l,3,5-tr iazine 대신 2_chloro_4,6_ diphenyl-l,3,5-triazine(21.7 g, 81.2 mmol) 을 사용한 것 외에는 합성예 1의 와 제조와 동일한 방법으로 화합물 X-ll(29.0 g, 수율 89 %; MS:[M+H]+=400)를 제조하였다. Instead of compound P-4, instead of di benzo [b, d] f uran-4-yl boron ic acid (17.2 g, 81.2 瞧 ol), 2-chloro-4,6-di henyl-l, 3,5-tr iazine Compound X-ll (29.0 g, yield 89%; MS: [M +] in the same manner as in Synthesis Example 1, except that 2_chloro_4,6_diphenyl-l, 3,5-triazine (21.7 g, 81.2 mmol) was used. H] + = 400).

Figure imgf000172_0003
Figure imgf000172_0003

화합물 R-4 대신 화합물 X-12(28.5 g, 71.3 醒 ol), 클로로포름 (200 ml), 아세트산 (200 ml), Br2(3.8 mL, 74.9隱 ol)을 사용한 것 외에는 합성예 20 의 화합물 R-5의 제조법과 동일한 방법으로 얻은 흔합물을 컬럼크로마토그래피로 실리카겔에서 핵산:에틸아세테이트 (10:1)로 정제하여 화합물 X-12(23.5 g, 수율 69 ； MS:[M+H]+= 478) 을 제조하였다. Synthesis example except for using compound X-12 (28.5 g, 71.3 醒 ol), chloroform (200 ml), acetic acid (200 ml), Br 2 (3.8 mL, 74.9 隱 ol) instead of compound R-4 The mixture obtained in the same manner as in the preparation of Compound R-5 of 20 was purified by column chromatography on silica gel with nucleic acid: ethyl acetate (10: 1) to give compound X-12 (23.5 g, yield 69; MS: [M + H] + = 478).

Figure imgf000173_0001
Figure imgf000173_0001

화합물 P-6 대신 화합물 X-12U8.2 g, 38.1 mmol), 2- 브로모페난트렌 (2— bromophenanthrene) 대신 t r i pheny 1 en-2-y 1 bor on i c acid(10.4 g, 38.1 隱 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 F(21.7 g, 수율 91 ； MS:[M+H]+= 626) 을 제조하였다. Compound X-12U8.2 g, 38.1 mmol) instead of compound P-6, tri pheny 1 en-2-y 1 bor on ic acid (10.4 g, 38.1 隱 ol) instead of 2-bromophenanthrene Compound F (21.7 g, Yield 91; MS: [M + H] + = 626) was prepared in the same manner as in Synthesis Example 1-1 except for using.

Figure imgf000173_0002
Figure imgf000173_0002

화합물 P-6 대신 화합물 X-12 18.2 g, 38.1 mmol), 2- 브로모페난트렌 (2— bromophenanthrene) 대신 [1，1'一 biphenyl]— 4— ylboronic acid(7.5 g, 38.1 隱 ol)을 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 GC19.8 g, 수율 94 %； MS:[M+H]+= 552) 을 제조하였다.

Figure imgf000174_0001
Instead of compound P-6, replace compound X-12 with 18.2 g, 38.1 mmol) and 2-bromophenanthrene with [1，1 '一 biphenyl] -4—ylboronic acid (7.5 g, 38.1 隱 ol). Compound GC19.8 g, yield 94%; MS: [M + H] + = 552) was prepared in the same manner as in Synthesis Example 1-1 except for use.
Figure imgf000174_0001

2-브로모페난트렌 (2-bromophenanthrene) 대신 2-브로모 -9,9- 다이메틸 -9H-플루오렌 (2-bromo-9,9-dime1;hyl-9H-fhK)rene)(10.4 g, 38.1 mmol)를 사용한 것 외에는 합성예 1-1과 동일한 방법으로 화합물 H(16.2 g, 수율 72 ； MS:[M+H]+=560) 을 제조하였다. 실시예 1 2-bromo-9,9-dimethyl-9H-fluorene (2-bromo-9,9-dime1; hyl-9H-fhK) rene) instead of 2-bromophenanthrene (10.4 g , 38.1 mmol), except that Compound H (16.2 g, yield 72; MS: [M + H] + = 560) was prepared in the same manner as in Synthesis Example 1-1. Example 1

IT0( indium tin oxide)가 1，300 A의 두께로 박막 코팅된 유리 기판을 세제를 녹인 증류수에 넣고 초음파로 세척하였다. 이때， 세제로는 피셔사 (Fischer Co.) 제품을 사용하였으며， 증류수로는 밀리포어사 (Millipore Co.) 제품의 필터 (Filter)로 2차로 걸러진 증류수를 사용하였다. IT0를 30분간 세척한 후 증류수로 2회 반복하여 초음파 세척을 10분간 진행하였다. 증류수 세척이 끝난 후， 이소프로필알콜， 아세톤， 메탄올의 용제로 초음파 세척을 하고 건조시킨 후 플라즈마 세정기로 수송시켰다. 또한， 산소 플라즈마를 이용하여 상기 기판을 5분간 세정한 후 진공 증착기로 기판을 수송시켰다.  A glass substrate coated with a thin film having an indium tin oxide (IT0) of 1,300 A was placed in distilled water in which a detergent was dissolved and ultrasonically cleaned. At this time, Fischer Co. product was used as the detergent, and distilled water filtered secondly as a filter of Millipore Co. product was used as the distilled water. After washing IT0 for 30 minutes, the ultrasonic cleaning was performed twice with distilled water for 10 minutes. After the distilled water wash, ultrasonic cleaning with a solvent of isopropyl alcohol, acetone, methanol, dried and transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.

상기와 같이 준비된 ΠΌ 투명 전극 위에 하기와 같은 HI-1 화합물을 50A의 두께로 열 진공 증착하여 정공 주입층을 형성하였다.  The HI-1 compound as described above was thermally vacuum deposited to a thickness of 50 A on the π transparent electrode prepared as above to form a hole injection layer.

상기 정공 주입층 위에 HT-1 화합물을 250 A의 두께로 열 진공 증착하여 정공 수송층을 형성하고， HT-1 증착막 위에 HT-2 화합물을 50 A 두께로 진공 증착하여 전자 저지층을 형성하였다.  A hole transport layer was formed by thermal vacuum deposition of the HT-1 compound at a thickness of 250 A on the hole injection layer, and an electron blocking layer was formed by vacuum deposition of the HT-2 compound at a thickness of 50 A on the HT-1 deposition film.

이어서， 상기 HT-2 증착막 위에 상기 합성예 1-1에서 제조한 화합물 1과 1¾의 중량비로 인광 도펀트 YGD-1을 공증착하여 400 A 두께의 발광층을 형성하였다. Subsequently, the compound prepared in Synthesis Example 1-1 on the HT-2 deposited film. Phosphorescent dopant YGD-1 was co-deposited at a weight ratio of 1 and 1¾ to form a light emitting layer having a thickness of 400 A.

상기 발광층 위에 ET-1 물질을 250 A의 두께로 진공 증착하고， 추가로 ET-2 물질을 100 A 두께로 2% 중량비의 Li과 공증착하여 전자 수송층 및 전자 주입층을 형성하였다. 상기 전자 주입층 위에 1000A 두께로 알루미늄을 증착하여 음극을 형성하였다.  An ET-1 material was vacuum deposited to a thickness of 250 A on the light emitting layer, and the ET-2 material was co-deposited with Li in a 2% weight ratio to a thickness of 100 A to form an electron transport layer and an electron injection layer. Aluminum was deposited to a thickness of 1000 A on the electron injection layer to form a cathode.

상기의 과정에서 유기물의. 증착속도는 0.4 ~ 0.7 A /sec를 유지하였고, 알루미늄은 2 A/sec의 증착 속도를 유지하였으며, 증착시 진공도는 1 X 10— 7 ~ 5 X 10— 8 torr를 유지하였다. Organic matter in the above process . The deposition rate was maintained at 0.4 ~ 0.7 A / sec, aluminum was deposited at a rate of 2 A / sec, the deposition, a vacuum was maintained to 1 X 10- 7 ~ 5 X 10- 8 torr.

Figure imgf000176_0001
Figure imgf000176_0001

Figure imgf000176_0002
LZ900/LlOZW^/13d 실시예 2 내지 실시예 49
Figure imgf000176_0002
LZ900 / LlOZW ^ / 13d Examples 2-49

발광층 형성시 인광 호스트 물질 및 도편트 함량을 하기 표 1 내지 3과 같이 변경하였다는 점을 제외하고는， 상기 실시예 1과 동일한 방법을 이용하여 실시예 2 내지 49의 유기 발광 소자를 각각 제작하였다. 비교예 1 내지 비교예 10  The organic light emitting diodes of Examples 2 to 49 were manufactured by the same method as Example 1, except that phosphorescent host materials and dopant contents were changed as shown in Tables 1 to 3 below to form the emission layer. . Comparative Example 1 to Comparative Example 10

발광층 형성시 인광호스트 물질 및 도펀트 함량을 하기 표 3과 같이 변경하였다는 점을 제외하고는， 상기 실시예 1과 동일한 방법을 이용하여 비교예 1 내지 10의 유기 발광 소자를 각각 제작하였다. 이때 비교예에 사용된 호스트 물질 A 내지 I는 하기와 같다. Except that the phosphorescent host material and the dopant content were changed as shown in Table 3 below, the organic light emitting diodes of Comparative Examples 1 to 10 were manufactured using the same method as in Example 1, respectively. In this case, the host materials A to I used in the comparative examples are as follows.

Figure imgf000178_0001
소자에 전류를 인가하여， 전압， 효율， 휘도, 색좌표 및 수명을 측정하고 그 결과를 하기 표 1 내지 3에 나타내었다. 이때， T95은 광밀도 50 mA/cm2에서의 초기 휘도를 100%로 하였을 때， 휘도가 95¾로 감소되는데 소요되는 시간을 의미한다.
Figure imgf000178_0001
By applying a current to the device, the voltage, efficiency, brightness, color coordinates and lifetime were measured and the results are shown in Tables 1 to 3 below. In this case, T95 means the time required to reduce the luminance to 95¾ when the initial luminance at the light density of 50 mA / cm 2 is 100%.

【표 1】  Table 1

호스트: 도펀트 전압 (V) 효율 (Cd/A) 색좌표 수명 (T95, h)Host: Dopant Voltage (V) Efficiency (Cd / A) Color Coordinate Life (T 95 , h)

No. No.

(두께, A)도펀트함량 (@10mA/cm2) (@10mA/cm2) (x,y) (@50mA/cm2) 실시예 화합물 1:YGD—1 (Thickness, A) Dopant content (@ 10 mA / cm 2 ) (@ 10 mA / cm 2 ) (x, y) (@ 50 mA / cm 2 ) Example Compound 1: YGD—1

2.99 62.8 (0.46,0.54) 47.5 1 (400)12%  2.99 62.8 (0.46,0.54) 47.5 1 (400) 12%

실시예 화합물 2:YGD-1 Example Compound 2: YGD-1

2.99 64.1 (0.46,0.53) 50.5 2 (400)12%  2.99 64.1 (0.46,0.53) 50.5 2 (400) 12%

실시예 화합물 3:YGD-1 Example Compound 3: YGD-1

2.97 65.0 (0.46,0.52) 47.0 3 (400)16%  2.97 65.0 (0.46,0.52) 47.0 3 (400) 16%

실시예 화합물 4:YGD-1 Example Compound 4: YGD-1

3.15 62.8 (0.46,0.53) 78.6 4 (400)12%  3.15 62.8 (0.46,0.53) 78.6 4 (400) 12%

실시예 화합물 5:YGD-1 Example Compound 5: YGD-1

3.11 53.8 (0.47,0.52) 46.4 5 (400)14%  3.11 53.8 (0.47,0.52) 46.4 5 (400) 14%

실시예 화합물 6:YGD— 1 Example Compound 6: YGD— 1

3.23 62.7 (0.47,0.53) 49.9 6 (400)12%  3.23 62.7 (0.47,0.53) 49.9 6 (400) 12%

실시예 화합물 7:YGD-1 Example Compound 7: YGD-1

3.20 . 63.1 (0.46,0.53) 50.3 7 (400)12%  3.20. 63.1 (0.46,0.53) 50.3 7 (400) 12%

실시예 화합물 8:YGD-1 Example Compound 8: YGD-1

3.30 55.7 (0.47,0.52) 87.9 8 (400)16%  3.30 55.7 (0.47,0.52) 87.9 8 (400) 16%

실시예 화합물 9:YGD-1 Example Compound 9: YGD-1

2.97 64.2 (0.46,0.54) 70.5 9 (400)16%  2.97 64.2 (0.46,0.54) 70.5 9 (400) 16%

실시예 화합물 10:YGD-1 Example Compound 10: YGD-1

3.12 60.3 (0.47,0.53) 47.7 10 (400)16%  3.12 60.3 (0.47,0.53) 47.7 10 (400) 16%

실시예 화합물 11:YGD-1 Example Compound 11: YGD-1

2.89 63.0 (0.46,0.53) 69.8 11 (400)16%  2.89 63.0 (0.46,0.53) 69.8 11 (400) 16%

실시예 화합물 14:YGD-1 Example Compound 14: YGD-1

3.08 56.1 (0.45,0.54) 47.6 12 (400)16%  3.08 56.1 (0.45,0.54) 47.6 12 (400) 16%

실시예 화합물 15:YGD-1 Example Compound 15: YGD-1

3.00 63.0 (0.46,0.53) 47.1 13 (400)12%  3.00 63.0 (0.46,0.53) 47.1 13 (400) 12%

실시예 화합물 16:YGD-1 Example Compound 16: YGD-1

3.28 . 63.2 (0.46,0.53) 41.8 14 (400)12%  3.28. 63.2 (0.46,0.53) 41.8 14 (400) 12%

실시예 화합물 12:YGD-1 Example Compound 12: YGD-1

3.55 65.9 (0.46,0.52) 126.2 15 (200:200)16%  3.55 65.9 (0.46,0.52) 126.2 15 (200: 200) 16%

실시예 화합물 13:PH-1:YGD-1 Example Compound 13: PH-1: YGD-1

3.51 67.2 (0.46,0.53) 116.0 16 (160:240)16%  3.51 67.2 (0.46,0.53) 116.0 16 (160: 240) 16%

실시예 화합물4:1 -2:¥01)一1 Example Compound 4: 1-2: ¥ 01) 一 1

3.57 67.7 (0.46,0.53) 191.9 17 (160:240)12%  3.57 67.7 (0.46,0.53) 191.9 17 (160: 240) 12%

실시예 화합물 Γ7:ΡΗ— 2:YGD-1 Example Compound Γ7: ΡΗ— 2: YGD-1

3.53 67.8 (0.47,0.53) 125.1 18 (200:200)16%  3.53 67.8 (0.47,0.53) 125.1 18 (200: 200) 16%

실시예 화합물18:1 -2:丫6[)一1 Example Compound 18: 1 -2: 丫 6 [ )一 1

3.56 70.2 (0.45,0.53) 132.8 19 (160:240)12%  3.56 70.2 (0.45,0.53) 132.8 19 (160: 240) 12%

실시예 화합물 19:PH-2:YGD-1 Example Compound 19: PH-2: YGD-1

3.50 68.9 (0.46,0.53) 352.0 3.50 68.9 (0.46,0.53) 352.0

20 - (200:200)15% 【표 2] 20-(200: 200) 15% [Table 2]

Figure imgf000180_0001
(두께， A)도편트함량 (@10mA/cm2) (@10mA/cm2) (x,y) (@50mA/cmz) 실시예 화합물 40:PH— 3:YGD— 1
Figure imgf000180_0001
(Thickness, A) Dopant content (@ 10 mA / cm 2 ) (@ 10 mA / cm 2 ) (x, y) (@ 50 mA / cm z ) Example Compound 40: PH— 3: YGD— 1

3.61 62.6 (0.44,0.54) 102.8 3.61 62.6 (0.44,0.54) 102.8

41 (200:200)16% 41 (200: 200) 16%

실시예 화합물 41:PH-2:YGD-1 Example Compound 41: PH-2: YGD-1

3.48 65.1 (0.47,0.53) 272.1 42 (160:240)16%  3.48 65.1 (0.47,0.53) 272.1 42 (160: 240) 16%

실시예 화합물 42:PH 2:YGD-1 Example Compound 42: PH 2: YGD-1

3.52 67.7 (0.45,0.54) 326.1 43 (160:240)12%  3.52 67.7 (0.45,0.54) 326.1 43 (160: 240) 12%

실시예 화합물 43:PH-3:YGD-1 Example Compound 43: PH-3: YGD-1

3.55 62.4 (0.45,0.53) 239.8 44 (160:240)12%  3.55 62.4 (0.45,0.53) 239.8 44 (160: 240) 12%

실시예 화합물 44:PH-3:YGD-1 Example Compound 44: PH-3: YGD-1

3.60 60.0 (0.46,0.52) 154.2 45 (200:200)16%  3.60 60.0 (0.46,0.52) 154.2 45 (200: 200) 16%

실시예 화합물 46:PH-1:YGD-1 Example Compound 46: PH-1: YGD-1

3.62 64.68 (0.45,0.53) 175.3 46 (160:240)16%  3.62 64.68 (0.45,0.53) 175.3 46 (160: 240) 16%

실시예 화합물 28:PH-2:YGD-1 Example Compound 28: PH-2: YGD-1

3.51 67.9 (0.45,0.54) 330.2 47 (160:240)16%  3.51 67.9 (0.45,0.54) 330.2 47 (160: 240) 16%

실시예 화합물 81:PH-2:YGD-1 Example Compound 81: PH-2: YGD-1

3.53 65.3 (0.47,0.54) 289.6 48 (160:240)12%  3.53 65.3 (0.47,0.54) 289.6 48 (160: 240) 12%

실시예 화합물 45:PH-2:YGD— 1 Example Compound 45: PH-2: YGD— 1

3.50 68.1 (0.45,0.52) 349.8 49 (160:240)12%  3.50 68.1 (0.45,0.52) 349.8 49 (160: 240) 12%

비교예 화합물 A:YGD-1 Comparative Example Compound A: YGD-1

3.21 61.9 (0.46,0.53) 25.9 1 (400)12%  3.21 61.9 (0.46,0.53) 25.9 1 (400) 12%

비교예 화합물 B:YGD-1 Comparative Example Compound B: YGD-1

3.17 56.2 (0.47,0.52) 27.3 2 (400)12%  3.17 56.2 (0.47,0.52) 27.3 2 (400) 12%

비교예 화합물 C:YGD-1 Comparative Example Compound C: YGD-1

2.92 62.2 (0.48,0.50) 20.3 3 (400)12%  2.92 62.2 (0.48,0.50) 20.3 3 (400) 12%

비교예 화합물 D:YGD-1 Comparative Example Compound D: YGD-1

3.11 67.3 (0.48,0.53) 26.2 4 (400)12%  3.11 67.3 (0.48,0.53) 26.2 4 (400) 12%

비교예 화합물 E:YGD-1 Comparative Example Compound E: YGD-1

4.73 28.11 (0.47,0.51) 22.2 4.73 28.11 (0.47,0.51) 22.2

5 (400)12% 5 (400) 12%

비교예 화합물 F:YGD-1 Comparative Example Compound F: YGD-1

3.15 53.2 (0.48,0.50) 27.5 6 (400)12%  3.15 53.2 (0.48,0.50) 27.5 6 (400) 12%

비교예 화합물 G:YGD-1 Comparative Example Compound G: YGD-1

3.14 52.7 (0.49,0.50) 26.9 7 (400)12%  3.14 52.7 (0.49,0.50) 26.9 7 (400) 12%

비교예 화합물 H:YGD-1 Comparative Example Compound H: YGD-1

' 3.14 56.8 (0.49,0.50) 28.9 8 (400)12%  '' 3.14 56.8 (0.49,0.50) 28.9 8 (400) 12%

비교예 화합물 I:YGD-1 Comparative Example Compound I: YGD-1

3.0 60 (0.46,0.53) 31.5 9 (400)12%  3.0 60 (0.46,0.53) 31.5 9 (400) 12%

비교예 화합물 A:PH— 1:YGD-1 Comparative Example Compound A: PH— 1: YGD-1

3.63 64.3 (0.47,0.53) 63.2 10 (160:240)16% 실시예 50  3.63 64.3 (0.47,0.53) 63.2 10 (160: 240) 16% Example 50

상기 실시예 1과 같이 준비된 ΠΌ 투명 전극 위에 하기와 같은 HI-1 화합물을 150A의 두께로 열 진공 증착하여 정공 주입층을 형성하였다.  On the πΌ transparent electrode prepared as in Example 1, a HI-1 compound as described below was thermally vacuum deposited to a thickness of 150 A to form a hole injection layer.

상기 정공 주입층 위에 HT-1 화합물을 1150A의 두께로' 열 진공증착하고， 순차적으로 HT-3 화합물을 500 A 두께로 진공 증착하여 정공 수송층을 형성하였다. HT-1 compound on the hole injection layer to the thickness of 1150A ' thermal vacuum deposition, and HT-3 compound to 500 A thickness by vacuum deposition sequentially A transport layer was formed.

이어서， 상기 정공수송층 위에 상기 합성예 15-3에서 제조한 화합물 47과 5%의 중량비로 인광 도펀트 GD-1을 공증착하여 400 A 두께의 발광층을 형성하였다.  Subsequently, phosphorescent dopant GD-1 was co-deposited on the hole transport layer at a weight ratio of Compound 47 and 5% prepared in Synthesis Example 15-3 to form a light emitting layer having a thickness of 400 A.

상기 발광층 위에 ET-3 물질을 50A의 두께로 진공 증착하여 정공저지층을 형성하고， 상기 정공저지층 위에 ET-4 물질 및 LiQ를 1 : 1의 중량비로 진공증착하여 250A의 전자 수송층을 형성하였다. 상기 전자 수송층 위에 순차적으로 10 A 두께의 리륨 프루라이드 (UF)를 증착하고， Mg을 10 >의 중량비로 Ag와 증착하여 200 A 두께로 전자주입층을 형성하였다. 이 위에 1000A 두께로 알루미늄을 증착하여 음극을 형성하였다.  A hole blocking layer was formed by vacuum depositing an ET-3 material to a thickness of 50 A on the light emitting layer, and a 250 A electron transport layer was formed by vacuum depositing an ET-4 material and LiQ in a weight ratio of 1: 1 on the hole blocking layer. . Lithium fluoride (UF) having a thickness of 10 A was sequentially deposited on the electron transport layer, and Mg was deposited with Ag at a weight ratio of 10> to form an electron injection layer having a thickness of 200 A. Aluminum was deposited to a thickness of 1000A on the cathode to form a cathode.

상기의 과정에서 유기물의 증착속도는 0.4 ~ 0.7 A/sec를 유지하였고， 음극의 리튬플루오라이드는 0.3 A/sec , 알루미늄은 2 A/sec의 증착 속도를 유지하였으며 , 증착시 진공도는 1 X 10— 7 ~ 5 x 10"8 torr를 In the above process, the deposition rate of the organic material was maintained at 0.4 to 0.7 A / sec, the lithium fluoride of the cathode was maintained at 0.3 A / sec, and the aluminum was maintained at the deposition rate of 2 A / sec. — 7 to 5 x 10 "8 torr

Figure imgf000182_0001
실시예 51 내지 실시예 90
Figure imgf000182_0001
Examples 51-90

발광층 형성시 인광 호스트 물질 및 도펀트 함량을 하기 표 4 및 5와 변경하였다는 점올 제외하고는， 상기 실시예 50과 동일한 방법을 이용하여 실시예 51 내지 90의 유기 발광 소자를 각각 제작하였다. 비교예 11 내지 비교예 19 Except for changing the phosphorescent host material and dopant content in forming the light emitting layer with Tables 4 and 5, the same method as in Example 50 was performed. Using each of the organic light emitting diodes of Examples 51 to 90, respectively. Comparative Examples 11 to 19

발광층 형성시 인광 호스트 물질 및 도펀트 함량을 하기 표 6과 같이 변경하였다는 점을 제외하고는， 상기 실시예 50과 동일한 방법을 이용하여 비교예 11 내지 19의 유기 발광 소자를 각각 제작하였다. 이때 비교예에 사용된 호스트 물질 A 내지 I는 상술한 바와 같다. 실험예 2  The organic light emitting diodes of Comparative Examples 11 to 19 were manufactured by the same method as Example 50, except that the phosphorescent host material and the dopant content were changed as shown in Table 6 when forming the emission layer. In this case, the host materials A to I used in the comparative examples are as described above. Experimental Example 2

상기 실시예 50 내지 90 및 비교예 11 내지 19에서 제작된 유기 발광 소자에 전류를 인가하여， 전압， 효율， 휘도， 색좌표 및 수명을 측정하고 그 결과를 하기 표 4 내지 6에 나타내었다. 이때， T95은 광밀도 20 mA/cm2에서의 초기 휘도를 100%로 하였을 때, 휘도가 95%로 감소되는데 소요되는 시간을 의미한다. The current was applied to the organic light emitting diodes manufactured in Examples 50 to 90 and Comparative Examples 11 to 19 to measure voltage, efficiency, brightness, color coordinate, and lifetime, and the results are shown in Tables 4 to 6 below. In this case, T95 means the time required for the luminance to decrease to 95% when the initial luminance at the light density of 20 mA / cm 2 is 100%.

【표 4】 Table 4

Figure imgf000183_0001
61 (400)5%
Figure imgf000183_0001
61 (400) 5%

실시예 화합물 56:GD-1 Example Compound 56: GD-1

3.99 52.4 (0.347,0.612) 51.3 62 (400)10%  3.99 52.4 (0.347, 0.612) 51.3 62 (400) 10%

실시예 화합물 4:PH-2:GD一 1 Example Compound 4: PH-2: GD 一 1

3.71 55.1 (0.351,0.609) 110.2 63 (200:200)5%  3.71 55.1 (0.351,0.609) 110.2 63 (200: 200) 5%

실시예 화합물 57:PH-3:GD-1 Example Compound 57: PH-3: GD-1

4.07 52.9 (0.348,0.612) 79.9 64 (200：200)5%  4.07 52.9 (0.348, 0.612) 79.9 64 (200: 200) 5%

실시예 화합물 58:PH-1:GD-1 Example Compound 58: PH-1: GD-1

4.2 51.7 (0.347,0.610) 88.7 65 (200:200)5%  4.2 51.7 (0.347,0.610) 88.7 65 (200: 200) 5%

실시예 화합물 6:PH-2:GD-1 Example Compound 6: PH-2: GD-1

4.21 53.4 (0.347,0.613) 100.1 66 (200:200)5%  4.21 53.4 (0.347,0.613) 100.1 66 (200: 200) 5%

실시예 화합물 50:PH-2:GD-1 Example Compound 50: PH-2: GD-1

4.17 58.1 (0.348,0.612) 78.9 67 (160:240)7%  4.17 58.1 (0.348,0.612) 78.9 67 (160: 240) 7%

실시예 화합물 60:PH-2:GD-1 Example Compound 60: PH-2: GD-1

4.23 51.7 (0.347,0.611) 89.2 68 (160:240)5%  4.23 51.7 (0.347,0.611) 89.2 68 (160: 240) 5%

실시예 화합물 61:PH— 3:GD-1 Example Compound 61: PH— 3: GD-1

4.11 54.2 (0.351,0.613) 106.2 69 (200：200)5%  4.11 54.2 (0.351, 0.613) 106.2 69 (200: 200) 5%

실시예 화합물 62:PH-2:GD-1 Example Compound 62: PH-2: GD-1

4.22 51.9 (0.351,0.613) 170.7 70 (160:240)5%  4.22 51.9 (0.351,0.613) 170.7 70 (160: 240) 5%

【표 5】 Table 5

호스트: 도펀트 전압 (V) 효율 (Cd/A) 색좌표 수명 (T95, h)Host: Dopant Voltage (V) Efficiency (Cd / A) Color Coordinate Life (T 95 , h)

No. No.

(두께， A)도편트함량 (@ 10mA/ cm2) (@10mA/cm2) (x,y) (@20mA/cm2) 실시예 화합물 63:PH-3:GD-1 (Thickness, A) Dopant content (@ 10 mA / cm 2 ) (@ 10 mA / cm 2 ) (x, y) (@ 20 mA / cm 2 ) Example Compound 63: PH-3: GD-1

. 4.31 54.2 (0.349,0.613) 134.9 71 (200:200)5%  . 4.31 54.2 (0.349,0.613) 134.9 71 (200: 200) 5%

실시예 화합물 64:PH-1:GD-1 Example Compound 64: PH-1: GD-1

4.30 54.3 (0.347,0.612) 135.4 72 (160:240)7%  4.30 54.3 (0.347, 0.612) 135.4 72 (160: 240) 7%

실시예 화합물 65:PH-2:GD-1 Example Compound 65: PH-2: GD-1

4.19 52.9 (0.351,0.613) 170.9 73 (200:200)5%  4.19 52.9 (0.351,0.613) 170.9 73 (200: 200) 5%

실시예 화합물66: ¾-1 1)-1 Example Compound 66: ¾-1 1) -1

3.92 52.3 (0.351,0.613) 171.4 74 (160:240)10%  3.92 52.3 (0.351,0.613) 171.4 74 (160: 240) 10%

실시예 화합물 67:PH-2:GD-1 Example Compound 67: PH-2: GD-1

4.12 .54.9 (0.350,0.611) 128.2 75 (200:200)5%  4.12 .54.9 (0.350,0.611) 128.2 75 (200: 200) 5%

실시예 화합물 68:PH-1:GD-1 Example Compound 68: PH-1: GD-1

3.76 56.8 (0.352,0.609) 104 76 (160:240)5%  3.76 56.8 (0.352,0.609) 104 76 (160: 240) 5%

실시예 화합물 69:PH-2:GD-1 Example Compound 69: PH-2: GD-1

4.10 55.1 (0.351,0.613) 103.2 77 (160:240)7%  4.10 55.1 (0.351,0.613) 103.2 77 (160: 240) 7%

실시예 화합물 70:PH-1:GD-1 Example Compound 70: PH-1: GD-1

4.17 56.53 (0.351,0.613) 104.5 78 (160:240)5%  4.17 56.53 (0.351,0.613) 104.5 78 (160: 240) 5%

실시예 화합물 71:PH-3:GD-1 Example Compound 71: PH-3: GD-1

4.24 54.6 (0.346,0.612) 137.9 79 (200:200)7%  4.24 54.6 (0.346,0.612) 137.9 79 (200: 200) 7%

실시예 화합물 72:PH— 2:GD-1 Example Compound 72: PH— 2: GD-1

4.32 56.1 (0.350,0.612) 158.8 80 (200:200)5%  4.32 56.1 (0.350,0.612) 158.8 80 (200: 200) 5%

실시예 화합물 73:PH-2:GD-1 Example Compound 73: PH-2: GD-1

4.42 51.24 (0.346,0.611) 102.5 81 (160:240)5%  4.42 51.24 (0.346,0.611) 102.5 81 (160: 240) 5%

실시예 화합물 74:PH— 2:GD-1 Example Compound 74: PH— 2: GD-1

4.13 54.7 (0.350,0.611) 119.9 82 (160:240)10%  4.13 54.7 (0.350,0.611) 119.9 82 (160: 240) 10%

실시예 화합물 75:PH— 3:GD一 1 Example Compound 75: PH— 3: GD 一 1

4.43 50.35 (0.346,0.613) 95.2 83 (200:200)7% 실시예 화합물 76:PH-3:GE L 4.43 50.35 (0.346,0.613) 95.2 83 (200: 200) 7% Example Compound 76: PH-3: GE L

4.14 52.8 (0.346,0.612) 105.7 4.14 52.8 (0.346, 0.612) 105.7

84 (160:240)10% 84 (160: 240) 10%

실시예 화합물 77:PH-1:GD-1  Example Compound 77: PH-1: GD-1

4.35 56.4 (0.347,0.611) 62.9 85 (200:200)5%  4.35 56.4 (0.347,0.611) 62.9 85 (200: 200) 5%

실시예 화합물78:^-1:61)一1  Example Compound 78: ^-1:61) I1

3.92 54 (0.352,0.609) 81.2 86 (200：200)5%  3.92 54 (0.352, 0.609) 81.2 86 (200: 200) 5%

실시예 화합물 79:PH-3:GD-1  Example Compound 79: PH-3: GD-1

4.16 56.13 (0.351,0.613) 104.3 87 (160:240)5%  4.16 56.13 (0.351,0.613) 104.3 87 (160: 240) 5%

실시예 화합물 80:PH— 1:GD-1  Example Compound 80: PH— 1: GD-1

4.32 50.89 (0.346,0.611) 100.4 88 (160:240)5%  4.32 50.89 (0.346,0.611) 100.4 88 (160: 240) 5%

실시예 화합물 59:PH-1:GD— 1  Example Compound 59: PH-1: GD— 1

4.29 53.7 (0.347,0.614) 92.6 89 (160:240)6%  4.29 53.7 (0.347,0.614) 92.6 89 (160: 240) 6%

실시예 화합물 45:PH-1:GD-1  Example Compound 45: PH-1: GD-1

4.31 57.3 (0.350,0.611) 168.1 90 (160:240)7%  4.31 57.3 (0.350,0.611) 168.1 90 (160: 240) 7%

【표 6] [Table 6]

Figure imgf000185_0001
상기 표 1 내지 6에서 보는 바와 같이， 본 발명에 따른 화합물을 인광 호스트 물질로 사용하여 제조된 유기 발광 소자의 경우에 비교예의 유기 발광 소자에 비하여 구동전압， 전류효율 및 수명 측면에서 우수한 성능을 나타냄을 확인할 수 있다. 특히， 실시예에 따른 유기 발광 소자는 통상적으로 사용되는 인광 호스트 물질인 화합물 I를 사용한 비교예 9 및 19에 따른 유기 발광 소자에 비하여 최소 150% 이상의 수명증가를 나타내었다. 또한, 실시예 4， 8 및 50에 따른 유기 발광 소자는 본 발명에 따른 화합물과 트리아지닐기의 치환 위치가 상이한 화합물 A 및 F를 각각 사용한 비교예 1， 6， 11 및 16에 따른 유기 발광 소자에 비하여 약 250% 이상의 수명 증가를 나타내었다. 그리고， 실시예 28에 따른 유기 발광 소자 또한， 화합물 C를 사용한 비교예 3에 따른 유기 발광 소자에 비하여 약 370% 이상의 수명 증가를 나타내었으며， 실시예 30 및 31에 따른 유기 발광 소자 또한, 화합물 G를 사용한 비교예 7에 따른 유기 발광 소자에 비하여 약 250% 이상의 수명 증가를 나타내었다. 추가적으로， 트리아지닐기가 포함되지 않은 화합물 E를 사용한 비교예 5에 따른 유기 발광 소자의 구동전압， 전류효율 및 수명은 실시예에 따른 유기 발광 소자에 비해 현저히 낮음을 알 수 있었다. 또한， 디메틸플루오레닐기가 치환된 화합물 H를 사용한 비교예 8 및 18에 따른 유기 발광 소자도 실시예에 따른 유기 발광 소자에 비하여 현저히 낮은 수명을 나타냄을 알 수 있는 데， 이는 소자 제작 시 또는 구동 중에 디메틸플루오레닐에 의한 라디칼이 형성됨에 따라 생성되는 불순물의 발생으로 인한 것으로 여겨진다.
Figure imgf000185_0001
As shown in Tables 1 to 6, the organic light emitting device manufactured by using the compound according to the present invention as a phosphorescent host material exhibits superior performance in terms of driving voltage, current efficiency, and lifetime compared to the organic light emitting device of the Comparative Example. can confirm. In particular, the organic light emitting device according to the embodiment is a phosphorescence that is commonly used The lifespan was increased by at least 150% compared to the organic light emitting diodes according to Comparative Examples 9 and 19 using the compound I as a host material. In addition, the organic light emitting device according to Examples 4, 8, and 50 is the organic light emitting device according to Comparative Examples 1, 6, 11, and 16 using compounds A and F having different substitution positions of the compound and triazinyl group according to the present invention, respectively. Compared with the lifespan increase of about 250% or more. In addition, the organic light emitting diode according to Example 28 also exhibited an increase in lifespan of about 370% or more compared to the organic light emitting diode according to Comparative Example 3 using the compound C. The organic light emitting diode according to Examples 30 and 31 also includes Compound G. Compared to the organic light emitting device according to Comparative Example 7, using the above, the lifespan was increased by about 250% or more. In addition, it was found that the driving voltage, current efficiency, and lifespan of the organic light emitting diode according to Comparative Example 5 using the compound E containing no triazinyl group were significantly lower than those of the organic light emitting diode according to the embodiment. In addition, it can be seen that the organic light emitting device according to Comparative Examples 8 and 18 using the compound H substituted with the dimethyl fluorenyl group also shows a significantly lower lifespan than the organic light emitting device according to the embodiment, which is used when manufacturing or driving the device. It is believed that this is due to the generation of impurities generated as radicals formed by dimethylfluorenyl in the air.

[부호의 설명】  [Explanation of code]

기판

Figure imgf000186_0001
Board
Figure imgf000186_0001

극  drama

발광층  Light emitting layer

정공 주입층 정공 수송층  Hole injection layer hole transport layer

발광층 전자 수송층  Emission Layer Electron Transport Layer

Claims

【청구범위】 [Claim] 【청구항 1]  [Claim 1] 하기 화학식 1로 표시되는 화합물:  Compound represented by the following formula (1):
Figure imgf000187_0001
Figure imgf000187_0001
 상기 화학식 1에서,  In Chemical Formula 1, Xi은 0또는 S이고,  Xi is 0 or S, Li 및 L2는 각각 독립적으로, 단일 결합; 치환 또는 비치환된 C6-60 아릴렌; 또는 치환 또는 비치환된 0 , N , Si 및 S로 구성되는 군으로부터 선택되는 헤테로원자를 1개 이상 포함하는 d-60 헤테로아릴렌이고， Li and L 2 are each independently a single bond; A substituted or unsubstituted C 6 - 60 arylene; Or d-60 heteroarylene containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted 0, N, Si, and S, - Yi 내지 Y3는 각각 독립적으로， Ν 또는 CR3이되， 내지 Y3 중 적어도 하나는 Ν이고 Yi to Y 3 are each independently N or CR 3 , at least one of Y 3 is N Arla및 Arlb는 각각 독립적으로， 치환 또는 비치환된 C6— 60 아릴; 또는 치환 또는 비치환된 N , 0 및 S로 구성되는 군으로부터 선택되는 헤테로원자를 1개 내지 3개 포함하는 d-60 헤테로아릴이고， Ar la and Ar lb are each independently a substituted or unsubstituted C 6 — 60 aryl; Or d-60 heteroaryl containing 1 to 3 heteroatoms selected from the group consisting of substituted or unsubstituted N, 0 and S, Ar2는 치환 또는 비치환된 C6-60 아릴이고, Ar 2 is substituted or unsubstituted C 6 -60 aryl, Ri 내지 R3는 각각 독립적으로， 수소; 중수소; 할로겐; 시아노; 니트로; 아미노; 치환 또는 비치환된 60 알킬; 치환 또는 비치환된 d-60 할로알킬 ; 치환 또는 비치환된 d-60 알콕시 ; 치환 또는 비치환된 Cwo 할로알콕시 ; 치환 또는 비치환된 C3-60 사이클로알킬; 치환 또는 비치환된Ri to R 3 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted 60 alkyl; Substituted or unsubstituted d-60 haloalkyl; Substituted or unsubstituted d-60 alkoxy; Substituted or unsubstituted Cwo haloalkoxy; Substituted or unsubstituted C 3 -60 cycloalkyl; Substituted or unsubstituted C2-60 알케닐; 치환 또는 비치환된 C6— 60 아릴 ; 치환 또는 비치환된 C6-60 아릴옥시; 또는 치환 또는 비치환된 N , 0 및 S로 구성되는 군으로부터 선택되는 헤테로원자를 1개 이상 포함하는 d-60 헤테로아릴이고， C 2 -60 alkenyl; Substituted or unsubstituted C 6 — 60 aryl; Substituted or unsubstituted C 6 -60 aryloxy; Or d-60 heteroaryl containing one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, 0 and S, nl 및 n2는 각각 독립적으로， 0 내지 3의 정수이다. nl and n2 are each independently an integer of 0-3. 【청구항 2】 [Claim 2] 제 1항에 있어서，  The method of claim 1, Li 및 L2는 각각 독립적으로， 단일 결합; 치환 또는 비치환된 페닐렌; 치환 또는 비치환된 나프틸렌; 또는 치환 또는 비치환된 바이페닐릴렌인， 화합물. Li and L 2 are each independently a single bond; Substituted or unsubstituted phenylene; Substituted or unsubstituted naphthylene; Or substituted or unsubstituted biphenylylene. 【청구항 3] [Claim 3] 제 1항에 있어서，  The method of claim 1, Li 및 L2는 각각 독립적으로, 단일 결합， 또는 하기로 구성되는 군으로 Li and L 2 are each independently a single bond or a group consisting of
Figure imgf000188_0001
Figure imgf000188_0001
 【청구항 4] [Claim 4] 제 1항에 있어서，  The method of claim 1, ^은 N이고, Y2는 Ν이고， Υ3는 Ν이거나; ^ Is N, Y 2 is Ν, Υ 3 is Ν; ^은 Ν이고, Υ2는 Ν이고， Υ3는 CH이거나; ^ Is Ν, Υ 2 is Ν, Υ 3 is CH; ^은 Ν이고， Υ2는 CH이고, Υ3는 Ν이거나; ^ Is an Ν, Υ 2 is CH, Υ is 3 or Ν; ^은^이고, Υ2는 CH이고， Υ3는 CH이거나; 또는 Yi은 CH이고， Y2는 CH이고， Y3는 Ν인 , 화합물 . ^ Is ^, Υ 2 is CH and Υ 3 is CH; or Yi is CH, Y 2 is CH and Y 3 is Ν. 【청구항 5] [Claim 5] 제 1항에 있어서，  The method of claim 1, Arla 및 는 각각 독립적으 하기로 구성되는 군으로부터 선택되는 어느 하나인， 화합물: Ar la and are each independently any one selected from the group consisting of:
Figure imgf000189_0001
Figure imgf000189_0001
 상기에서，  Above ¾는 0， S, NZ4 , 또는 CZ5Z6이고， ¾ is 0, S, NZ 4 , or CZ 5 Z 6 , Zi 내지 ¾은 각각 독립적으로， 수소; 증수소; 할로겐; 시아노; 니트로; 아미노; 치환 또는 비치환된 d-20 알킬 ; 치환 또는 비치환된 d-20 할로알킬 ; 치환 또는 비치환된 C6-20 아릴 ; 또는 치환 또는 비치환된 N, 0 및 S로 구성되는 군으로부터 선택되는 헤테로원자를 1개 이상 포함하는 d-20 헤테로아릴이고， Zi to ¾ are each independently hydrogen; Distillate; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d- 20 alkyl; Substituted or unsubstituted d- 20 haloalkyl; Substituted or unsubstituted C 6 - 20 aryl; Or d- 20 heteroaryl including one or more heteroatoms selected from the group consisting of substituted or unsubstituted N, 0 and S, cl은 0 내지 5의 정수이고,  cl is an integer from 0 to 5, c2는 0 내지 4의 정수이고,  c2 is an integer of 0 to 4, c3는 0 내지 3의 정수이다.  c3 is an integer of 0-3. 【청구항 6】 [Claim 6] 제 5항에 있어서，  The method of claim 5, Arla 및 Arlb는 각각 독립적으로， 하기로 구성되는 군으로부터 선택되는 어느 하나인, 화합물: 681 Ar la and Ar lb are each independently any one selected from the group consisting of: 681
Figure imgf000190_0001
Figure imgf000190_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000191_0001
Figure imgf000191_0001
 【청구항 7] [Claim 7] 제 1항에 있어서，  The method of claim 1, Ar2는 하기로 구성되는 군으로부터 선택되는 어느 하나인， 화합물: T6T Ar 2 is any one selected from the group consisting of: T6T
Figure imgf000192_0001
Figure imgf000192_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000193_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000193_0001
 상기에서,  In the above, Zn 내지 Ζ14는 각각 독립적으로, 수소; 중수소; 할로겐; 시아노; 니트로 ; 아미노; 치환 또는 비치환된 d-60 알킬 ; 치환 또는 비치환된 d-60 할로알킬; Si (Qi) (Q2) (Q3) ; C(Q4) (Q5) (Q6) 및 C6-60 아릴이고， Zn to X 14 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-60 alkyl; Substituted or unsubstituted d-60 haloalkyl; Si (Qi) (Q 2 ) (Q 3 ); C (Q 4 ) (Q 5 ) (Q 6 ) and C 6 -60 aryl, 여기서， ¾ 내지 Q6은 각각 독립적으로， 수소; 중수소; 할로겐; 시아노 ; 니트로 ; 아미노; 치환 또는 비치환된 d-20 알킬 ; 또는 치환 또는 비치환된 C6-20 아릴 0 1고， Here, ¾ to Q 6 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted d-20 alkyl; Or a substituted or unsubstituted C 6 - 20 aryl and 0, 1, cll은 0 내지 5의 정수이고，  cll is an integer from 0 to 5, cl2는 0 내지 7의 정수이고，  cl2 is an integer of 0 to 7, cl3는 0 내지 9의 정수이고，  cl3 is an integer of 0 to 9, cl4는 0 내지 4의 정수이고，  cl4 is an integer of 0 to 4, cl5는 0 내지 3의 정수이고，  cl5 is an integer of 0 to 3, cl6은 0 내지 11의 정수이고  cl6 is an integer from 0 to 11 cl7은 0 내지 9의 정수이고，  cl7 is an integer of 0 to 9, cl8은 0 내지 6의 정수이고，  cl8 is an integer from 0 to 6, cl9는 0 내지 12의 정수이다  cl9 is an integer from 0 to 12 【청구항 8】 [Claim 8] 게 7항에 있어서，  According to claim 7, Ar2는 하기로 구성되는 군으로부터 선택되 어느 하나인， 화합물: £61 Ar 2 is any one selected from the group consisting of: £ 61
Figure imgf000194_0001
Figure imgf000194_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV f6l LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV f6l
Figure imgf000195_0001
Figure imgf000195_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000196_0001
Figure imgf000196_0001
 【청구항 9] [Claim 9] 제 1항에 있어서,  The method of claim 1, Ri 및 R2는 각각 독립적으로, 수소; 중수소; 시아노; 또는 치환 또 비치환된 ( 10 알킬인， 화합물 . Ri and R 2 are each independently hydrogen; heavy hydrogen; Cyano; Or substituted or unsubstituted ( 10 alkyl. 【청구항 10] [Claim 10] 제 1항에 있어서，  The method of claim 1, 상기 화합물은 하기 화합물로 구성되는 군으로부터 선택되는 어 하나인， 화합물: 961 The compound is one selected from the group consisting of the compounds, 961
Figure imgf000197_0001
Figure imgf000197_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV Λ6Ι LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV Λ6Ι
Figure imgf000198_0001
Figure imgf000198_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 861 LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 861
Figure imgf000199_0001
Figure imgf000199_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 661 LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 661
Figure imgf000200_0001
Figure imgf000200_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV ooz LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV ooz
Figure imgf000201_0001
Figure imgf000201_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000202_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV zoz
Figure imgf000202_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV zoz
Figure imgf000203_0001
Figure imgf000203_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000204_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000204_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000205_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 0Z
Figure imgf000205_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 0Z
Figure imgf000206_0001
Figure imgf000206_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 90Z LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 90Z
Figure imgf000207_0001
Figure imgf000207_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LOZ LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV LOZ
Figure imgf000208_0001
Figure imgf000208_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 80Z LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 80Z
Figure imgf000209_0001
Figure imgf000209_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000210_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000210_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000211_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000211_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000212_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000212_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000213_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000213_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000214_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000215_0001
SIC
Figure imgf000214_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000215_0001
SIC
Figure imgf000216_0001
Figure imgf000216_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000217_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LIZ
Figure imgf000217_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV LIZ
Figure imgf000218_0001
Figure imgf000218_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 21Z LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 21Z
Figure imgf000219_0001
Figure imgf000219_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 61 Z LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 61 Z
Figure imgf000220_0001
Figure imgf000220_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV ozz LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV ozz
Figure imgf000221_0001
Figure imgf000221_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000222_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV zzz
Figure imgf000222_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV zzz
Figure imgf000223_0001
Figure imgf000223_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000224_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000224_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000225_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000225_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000227_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZZ
Figure imgf000227_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV LZZ
Figure imgf000228_0001
Figure imgf000228_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV ZZ LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV ZZ
Figure imgf000229_0001
Figure imgf000229_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000230_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000230_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000231_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000231_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000232_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000232_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000233_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000233_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000234_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000234_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000235_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV £Z
Figure imgf000235_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV £ Z
Figure imgf000236_0001
Figure imgf000236_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV 9£Z LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV 9 £ Z
Figure imgf000237_0001
Figure imgf000237_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZZ LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV LZZ
Figure imgf000238_0001
Figure imgf000238_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV £Z LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV £ Z
Figure imgf000239_0001
Figure imgf000239_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000240_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV
Figure imgf000240_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000241_0001
LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV IfZ
Figure imgf000241_0001
LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV IfZ
Figure imgf000242_0001
Figure imgf000242_0001
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000243_0001
Figure imgf000243_0001
Figure imgf000243_0002
Figure imgf000243_0002
 LZ900/LlOZW^/13d Ζ1^9ΐΟ/8ΐΟΖ OAV LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
Figure imgf000244_0001
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LZ900 / LlOZW ^ / 13d Ζ1 ^ 9ΐΟ / 8ΐΟΖ OAV
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Figure imgf000250_0001
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 【청구항 HI Claim Port HI 게 1 전극; 상기 제 1 전극과 대향하여 구비된 제 2 전극; 및 상기 제 1 전극과 상기 제 2 전극 사이에 구비된 1층 이상의 유기물 층을 포함하는 유기 발광 소자로서 , 상기 유기물 층 중 1층 이상은 제 1항 내지 제 10항 중 어느 하나의 항에 따른 화합물을 포함하는 것인， 유기 발광소자.  Crab 1 electrode; A second electrode provided to face the first electrode; And at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers is a compound according to any one of claims 1 to 10. That comprises a, organic light emitting device. 【청구항 12】 [Claim 12] 제 11항에 있어서，  The method of claim 11, 상기 화합물을 포함하는 유기물층은 발광층인， 유기 발광 소자. 【청구항 13] The organic material layer containing the compound is a light emitting layer, an organic light emitting device. [Claim 13] 제 12항에 있어서，  The method of claim 12, 상기 화합물은 호스트 물질로 사용되는， 유기 발광 소자.  The compound is used as a host material, an organic light emitting device.
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