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WO2013168927A2 - Novel compound and organic electroluminescent device comprising same - Google Patents

Novel compound and organic electroluminescent device comprising same Download PDF

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Publication number
WO2013168927A2
WO2013168927A2 PCT/KR2013/003806 KR2013003806W WO2013168927A2 WO 2013168927 A2 WO2013168927 A2 WO 2013168927A2 KR 2013003806 W KR2013003806 W KR 2013003806W WO 2013168927 A2 WO2013168927 A2 WO 2013168927A2
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group
formula
mat
aryl
compound
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Korean (ko)
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WO2013168927A3 (en
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김태형
배형찬
손효석
백영미
박호철
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Doosan Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
    • C07D491/14—Ortho-condensed systems
    • C07D491/147—Ortho-condensed systems the condensed system containing one ring with oxygen as ring hetero atom and two rings with nitrogen as ring hetero atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/12—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains three hetero rings
    • C07D495/14—Ortho-condensed systems
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    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C—CHEMISTRY; METALLURGY
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    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/008—Triarylamine dyes containing no other chromophores
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    • 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
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • 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
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1048—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with oxygen
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C09K2211/1051—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms with sulfur
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • C09K2211/1066—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms with sulfur

Definitions

  • the present invention relates to a novel compound and an organic electroluminescent device comprising the same.
  • the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to achieve better natural colors, depending on the light emission color.
  • a host / dopant system may be used as the light emitting material.
  • the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
  • a metal complex compound containing heavy atoms such as Ir and Pt.
  • NPB, BCP, Alq 3 and the like are widely known as materials used for the hole injection layer and the electron transport layer, and anthracene derivatives are used as the light emitting material.
  • a metal complex compound including Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 is used as a blue, green, or red phosphorescent dopant material, and CBP is used as a phosphorescent host material.
  • the conventional light emitting materials have good light emission characteristics, they are not satisfactory in terms of lifespan of the organic EL device, and thus, development of a light emitting material having excellent performance is required.
  • an object of the present invention is to provide a novel compound and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.
  • the present invention provides a compound represented by the following formula (1).
  • A is O (oxygen) or S (sulfur)
  • X 1 to X 4 are each independently CR 1 or N (nitrogen)
  • Y 1 and Y 2 , Y 2 and Y 3 are independently CR 1 or N (nitrogen)
  • Y 1 and Y 2 , Y 2 and Y 3 are independently CR 1 or N (nitrogen)
  • Y 1 and Y 2 , Y 2 and Y 3 are each independently CR 1 or N (nitrogen)
  • One of Y 3 and Y 4 forms a condensed ring with the compound represented by Formula 2
  • one of Y 1 to Y 4 that does not form a condensed ring is CR 2 or N (nitrogen), wherein N (nitrogen) Must contain at least one
  • Z 1 to Z 4 are each independently CR 3 or N (nitrogen),
  • R 1 to R 3 are each independently hydrogen, deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6- C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 arylamine group, (C 6 - of C 40 aryl) C of 1 - C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ⁇ C 40 alkyl silyl group, and a C 6 ⁇ C 40 of Selected from the group consisting of arylsilyl groups, may be bonded to adjacent groups to form a condensed ring,
  • Ar 1 is hydrogen, C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 40 Aryl group, nuclear atoms 5 to 40 heteroaryl C 6 -C 40 aryloxy group, C 1 -C 40 alkyloxy group, C 6 -C 40 arylamine group, (C 6 -C 40 aryl) C 1 -C 40 alkyl group, C 3 ⁇ C 40 of is selected from cycloalkyl groups, 3 to 40 nuclear atoms heterocycloalkyl group, the group consisting of C 1 ⁇ C 40 alkyl silyl group, and a C 6 ⁇ C 40 aryl group in the silyl.
  • R 1 to R 3 may combine with an adjacent group to form a condensed ring (condensed aliphatic ring, condensed aromatic ring, condensed heteroaliphatic ring, condensed heteroaromatic ring, or a combination thereof).
  • the silyl group and the arylsilyl group are deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 40 aryl group, nucleus Heteroaryl group of 5 to 40 atoms, C 6 to C 40 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 40 arylamine group, (C 6 to C 40 aryl) C 1 ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group, nuclear atoms, 3 to 40 hetero
  • Alkyl in the present invention means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms.
  • alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.
  • Alkenyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond.
  • alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.
  • Alkynyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond.
  • alkynyl include, but are not limited to, ethynyl, 2-propynyl, and the like.
  • Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, a single ring or a combination of two or more rings, and may also include a form in which two or more rings are simply attached or condensed with each other.
  • Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.
  • Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon of 5 to 40 nuclear atoms (number of atoms including carbon), at least one carbon in the ring, Preferably one to three carbons are substituted with heteroatoms such as N, O, S or Se.
  • Heteroaryl can be interpreted that two or more rings may be attached in a simple or fused form with each other, and also include a condensed form with an aryl group.
  • heteroaryl examples include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
  • Aryloxy in the present invention is a monovalent substituent represented by RO-, wherein R is aryl having 6 to 60 carbon atoms.
  • R is aryl having 6 to 60 carbon atoms.
  • Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy and the like.
  • Alkyloxy in the present invention is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure It can be interpreted as being included.
  • alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
  • Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
  • Cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms.
  • Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
  • Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O or S and Are substituted with the same hetero atom.
  • heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
  • Alkylsilyl in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms
  • arylsilyl means silyl substituted with aryl having 6 to 40 carbon atoms.
  • the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device characterized in that it comprises a.
  • the organic material layer including the compound represented by Formula 1 is preferably a light emitting layer.
  • the compound represented by Formula 1 when the compound represented by Formula 1 is a light emitting layer, the compound represented by Formula 1 may be a blue, green or red phosphorescent host material.
  • the present invention not only has a higher molecular weight than the conventional organic electroluminescent device material (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')), but also has a wide energy band gap, It is a feature to provide a compound represented by the formula (1) that can increase the binding force.
  • 'CBP' 4,4-dicarbazolybiphenyl
  • a heterocyclic moiety preferably an indole derivative moiety (moiety) is bonded to the end of benzothienopyridine or benzofuropyridine Fused). Since the benzothienopyridine or benzofuropyridine skeleton has a high triplet energy level, when the compound represented by Formula 1 of the present invention is used in an organic electroluminescent device, the phosphorescence characteristics of the device are improved. At the same time, the hole injection ability, hole transport ability, luminous efficiency, driving voltage, and lifetime characteristics can be improved.
  • the compound represented by Formula 1 of the present invention has a wide bandgap (sky blue to red) due to the indole derivative moiety bound to the terminal of the benzocyanopyridine or benzofuropyridine skeleton, Since the bonding force can be increased, it can exhibit excellent properties as a host material of the light emitting layer, specifically, a blue, green and / or red phosphorescent host material, compared to the conventional CBP.
  • the compound represented by the formula (1) of the present invention exhibits a high glass transition temperature because a variety of substituents (R 1 to R 3 and Ar 1 ) is bonded to significantly increase the molecular weight of the compound, which is higher than the conventional CBP May have thermal stability.
  • the portion of the Y 1 to Y 4 that does not form a condensed ring preferably contains one or more N.
  • all of X 1 to X 4 are CR 1 or include one or more N, and all of Z 1 to Z 4 are preferably CR 3 or one or more N.
  • Ar 1 substituted in the indole derivative moiety is preferably a C 6 ⁇ C 40 aryl group or a heteroaryl group of 5 to 40 nuclear atoms.
  • the aryl group or heteroaryl group of Ar 1 Deuterium, halogen, cyano group, C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 40 the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C 6 ⁇ C 40 aryloxy group, alkyloxy group of C 1 ⁇ C 40 of, C 6 ⁇ C 40 aryl amine group, a (C 6 ⁇ C 40 aryl) C 1 to C 40 alkyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group and C 6 to C 40 arylsilyl It may be substituted with one or more substituents selected from the group consisting of groups, and when having a plurality of substituents, each substituent may be the same or different.
  • R 1 to R 3 and Ar 1 which are substituents (functional groups) of the compound represented by Formula 1 of the present invention include the following examples (S1 to S138), but are not limited thereto.
  • Ar 1 in the substituent (functional group) of the compound represented by Formula 1 of the present invention is preferably selected from the group consisting of structures represented by S-1 to S-39.
  • the compound represented by Chemical Formula 1 of the present invention is preferably selected from the group consisting of compounds represented by the following Chemical Formulas 3 to 8, but is not limited thereto.
  • the compound represented by Formula 1 of the present invention is preferably selected from the group consisting of compounds represented by the following Formulas C1 to C18, but is not limited thereto.
  • A is more preferably S.
  • Specific examples of the compound represented by Formula 1 of the present invention include the following compounds (C-1 to C-578), but is not limited thereto.
  • Such a compound represented by Formula 1 of the present invention can be synthesized in various ways with reference to the synthesis process of the following examples.
  • the present invention provides an organic electroluminescent device comprising a compound represented by Chemical Formula 1, preferably a compound represented by Chemical Formulas 3 to 8.
  • the present invention provides an organic electroluminescent device comprising an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is represented by Formula 1 above.
  • the compound represented Preferably the compound represented by Formula 3-8 is included. In this case, the compounds represented by Formulas 3 to 8 may be used alone or in combination of two or more.
  • the one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, preferably a hole injection layer, a hole transport layer, a light emitting layer or an electron transport layer, more preferably It may be a light emitting layer.
  • the organic electroluminescent device may include a host material in the light emitting layer.
  • the compound represented by Formula 1 may be used as the host material.
  • the compound represented by Chemical Formula 1 is used as a light emitting layer of the organic EL device, preferably a blue, green or red phosphorescent host material of the light emitting layer, the binding force between the holes and the electrons in the light emitting layer is increased, so that the efficiency of the organic EL device is increased. (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved.
  • the structure of the organic electroluminescent device of the present invention is not particularly limited, but may be formed of a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode are sequentially stacked.
  • the electron injection layer may be further stacked on the electron transport layer.
  • the organic electroluminescent device according to the present invention may not only have a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, but also a structure in which an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.
  • the material that can be used as the anode included in the organic electroluminescent device according to the present invention is not particularly limited, but non-limiting examples include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black and the like can be used.
  • metals such as vanadium, chromium, copper, zinc, gold or alloys thereof
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2
  • the material usable as the negative electrode included in the organic electroluminescent device according to the present invention is not particularly limited, but non-limiting examples include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, Or metals such as lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • the organic material layer included in the organic electroluminescent device according to the present invention is known in the art except for using the compound represented by Formula 1 in any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer It can be made of a material.
  • the material usable as the substrate included in the organic electroluminescent device according to the present invention is not particularly limited, but non-limiting examples may include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.
  • Such an organic electroluminescent device of the present invention may be manufactured by a method known in the art, the light emitting layer included in the organic material layer may be manufactured by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • a CORE2-B 6g (yield: 67%) was obtained in the same manner as in ⁇ Step 1> of Preparation Example 1, except that CORE2-A was used instead of CORE1-A-1.
  • the compound Mat-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was manufactured as follows.
  • a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 ⁇ was washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.
  • ITO Indium tin oxide
  • Example 2 The same procedure as in Example 1 was repeated except that the compounds Mat-2 to Mat-34 synthesized in Synthesis Examples 2 to 34 were used instead of the compound Mat-1 to be used as the light emitting host material in Example 1 To produce a green organic electroluminescent device.
  • a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound Mat-1 used as the light emitting host material in forming the light emitting layer in Example 1.
  • the structure of CBP used is as follows.
  • Example 1 Sample Host Drive voltage (V) Emission Peak (nm) Current efficiency (cd / A) Example 1 Mat-1 6.50 520 41.0 Example 2 Mat-2 6.61 523 41.2 Example 3 Mat-3 6.60 523 40.8 Example 4 Mat-4 6.58 523 41.1 Example 5 Mat-5 6.70 522 41.8 Example 6 Mat-6 6.70 520 41.3 Example 7 Mat-7 6.51 521 41.4 Example 8 Mat-8 6.66 520 40.9 Example 9 Mat-9 6.50 520 41.0 Example 10 Mat-10 6.45 519 41.5 Example 11 Mat-11 6.60 521 41.3 Example 12 Mat-12 6.55 518 41.1 Example 13 Mat-13 6.70 520 41.2 Example 14 Mat-14 6.50 523 41.3 Example 15 Mat-15 6.64 520 41.1 Example 16 Mat-16 6.60 522 41.5 Example 17 Mat-17 6.62 522 40.9 Example 18 Mat-18 6.70 520 41.4 Example 19 Mat-19 6.64 520 41.0 Example 20 Mat-20 6.50 521 41.6 Example 21 Mat-21 6.70 520 41.5 Example 22 Mat-22 6.63 521 41.0 Example 23 Mat-23 6.70
  • the green organic electroluminescent devices manufactured in Examples 1 to 34 which use the compounds represented by Chemical Formula 1 of the present invention (Compounds Mat-1 to Mat-34) as the host material of the emission layer, respectively, have conventional CBP. It was confirmed that the green organic electroluminescent device of Comparative Example 1 used exhibited superior performance in terms of current efficiency and driving voltage.
  • the efficiency (luminescence efficiency and messenger efficiency), lifetime, brightness and driving of the organic electroluminescent device Voltage and the like can be improved. Accordingly, the present invention can provide a full color organic electroluminescent panel with improved performance and lifespan.

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Description

신규 화합물 및 이를 포함하는 유기 전계 발광 소자New compound and organic electroluminescent device comprising same

본 발명은 신규 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to a novel compound and an organic electroluminescent device comprising the same.

유기 전계 발광 소자는 두 전극 사이에 전압을 걸어 주면 양극에서 정공이, 음극에서 전자가 유기물층으로 주입되어, 주입된 정공과 전자가 만나 엑시톤(exciton)이 형성되며, 형성된 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 유기물층으로 사용되는 물질은 기능에 따라, 발광 물질, 정공 주입 물질, 정공 수송 물질, 전자 수송 물질, 전자 주입 물질 등으로 분류될 수 있다.When an organic electroluminescent device applies a voltage between two electrodes, holes are injected from the anode and electrons are injected into the organic material layer from the cathode. When the injected holes and the electrons meet to form an exciton, the formed excitons fall to the ground state. The light will shine. The material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to a function.

발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질과 보다 나은 천연색을 구현하기 위해 필요한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통해 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도판트 계를 사용할 수 있다.The light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to achieve better natural colors, depending on the light emission color. In addition, in order to increase luminous efficiency through increasing color purity and energy transfer, a host / dopant system may be used as the light emitting material.

도판트 물질은 유기 물질을 사용하는 형광 도판트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도판트로 나눌 수 있다. 인광 도판트의 개발은 이론적으로 형광 도판트에 비해 4배까지 발광 효율을 향상 시킬 수 있어 인광 도판트 뿐만 아니라 인광 호스트에 대해서도 연구되고 있다.The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. The development of phosphorescent dopants is theoretically able to improve luminous efficiency up to 4 times compared to fluorescent dopants, so research is being conducted not only on phosphorescent dopants but also on phosphorescent hosts.

현재까지 정공 수송층. 정공 주입층, 전자 수송층 등으로 사용되는 물질로는 NPB, BCP, Alq3 등이 널리 알려져 있으며, 발광 물질로는 안트라센 유도체들이 사용되고 있다. 구체적으로 발광 물질 중 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물은 blue, green 또는 red 인광 도판트 재료로, CBP는 인광 호스트 재료로 사용되고 있다.Hole transport layer to date. NPB, BCP, Alq 3 and the like are widely known as materials used for the hole injection layer and the electron transport layer, and anthracene derivatives are used as the light emitting material. Specifically, a metal complex compound including Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 is used as a blue, green, or red phosphorescent dopant material, and CBP is used as a phosphorescent host material. .

그러나 종래의 발광 물질들은 발광 특성이 양호하나, 유기 전계 발광 소자의 수명측면에서 만족할만한 수준이 되지 못하기 때문에 우수한 성능을 가지는 발광 물질의 개발이 요구되고 있다.However, although the conventional light emitting materials have good light emission characteristics, they are not satisfactory in terms of lifespan of the organic EL device, and thus, development of a light emitting material having excellent performance is required.

본 발명은 상기한 문제점을 해결하기 위해, 유기 전계 발광 소자의 효율, 수명 및 안정성 등을 향상시킬 수 있는 신규 화합물 및 상기 화합물을 이용한 유기 전계 발광 소자를 제공하는 것을 목적으로 한다.In order to solve the above problems, an object of the present invention is to provide a novel compound and an organic electroluminescent device using the compound which can improve the efficiency, lifespan and stability of the organic electroluminescent device.

상기한 목적을 달성하기 위해 본 발명은, 하기 화학식 1로 표시되는 화합물을 제공한다.In order to achieve the above object, the present invention provides a compound represented by the following formula (1).

[화학식 1][Formula 1]

Figure PCTKR2013003806-appb-I000001
Figure PCTKR2013003806-appb-I000001

상기 화학식 1에서, A는 O(산소) 또는 S(황)이고, X1 내지 X4는, 각각 독립적으로, CR1 또는 N(질소)이고, Y1과 Y2, Y2와 Y3, Y3와 Y4 중 하나는 하기 화학식 2로 표시되는 화합물과 축합 고리를 형성하고, Y1 내지 Y4 중 축합 고리를 형성하지 않는 것은 CR2 또는 N(질소)이고, 이때, N(질소)를 반드시 하나 이상 포함하며,In Formula 1, A is O (oxygen) or S (sulfur), X 1 to X 4 are each independently CR 1 or N (nitrogen), Y 1 and Y 2 , Y 2 and Y 3 , One of Y 3 and Y 4 forms a condensed ring with the compound represented by Formula 2, and one of Y 1 to Y 4 that does not form a condensed ring is CR 2 or N (nitrogen), wherein N (nitrogen) Must contain at least one

[화학식 2][Formula 2]

Figure PCTKR2013003806-appb-I000002
Figure PCTKR2013003806-appb-I000002

상기 화학식 2에서, Z1 내지 Z4는, 각각 독립적으로, CR3 또는 N(질소)이고,In Chemical Formula 2, Z 1 to Z 4 are each independently CR 3 or N (nitrogen),

상기 R1 내지 R3는, 각각 독립적으로, 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, (C6~C40의 아릴)C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고, 인접하는 기와 서로 결합하여 축합 고리를 형성할 수 있으며,R 1 to R 3 are each independently hydrogen, deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6- C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, (C 6 - of C 40 aryl) C of 1 - C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, and a C 6 ~ C 40 of Selected from the group consisting of arylsilyl groups, may be bonded to adjacent groups to form a condensed ring,

상기 Ar1은 수소, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, (C6~C40의 아릴)C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된다.Ar 1 is hydrogen, C 1 ~ C 40 Alkyl group, C 2 ~ C 40 Alkenyl group, C 2 ~ C 40 Alkynyl group, C 6 ~ C 40 Aryl group, nuclear atoms 5 to 40 heteroaryl C 6 -C 40 aryloxy group, C 1 -C 40 alkyloxy group, C 6 -C 40 arylamine group, (C 6 -C 40 aryl) C 1 -C 40 alkyl group, C 3 ~ C 40 of is selected from cycloalkyl groups, 3 to 40 nuclear atoms heterocycloalkyl group, the group consisting of C 1 ~ C 40 alkyl silyl group, and a C 6 ~ C 40 aryl group in the silyl.

여기서, 상기 R1 내지 R3는 인접하는 기와 결합하여 축합 고리(축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합)를 형성할 수 있다.Here, R 1 to R 3 may combine with an adjacent group to form a condensed ring (condensed aliphatic ring, condensed aromatic ring, condensed heteroaliphatic ring, condensed heteroaromatic ring, or a combination thereof).

또한, 상기 R1 내지 R3 및 Ar1의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 아릴알킬기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기 및 아릴실릴기는, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, (C6~C40의 아릴)C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환 또는 비치환될 수 있으며, 복수개의 치환기를 가질 경우, 각각의 치환기는 동일하거나 상이할 수 있다.In addition, the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, arylalkyl group, cycloalkyl group, heterocycloalkyl group, alkyl of R 1 to R 3 and Ar 1 The silyl group and the arylsilyl group are deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6 -C 40 aryl group, nucleus Heteroaryl group of 5 to 40 atoms, C 6 to C 40 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 40 arylamine group, (C 6 to C 40 aryl) C 1 ~ C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, nuclear atoms, 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group and a C 6 ~ C 40 aryl silyl group selected from the group consisting of It may be substituted or unsubstituted with one or more substituents, and in the case of having a plurality of substituents, each substituent may be the same or different.

본 발명에서의 알킬은 탄소수 1 내지 40의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알킬의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등을 들 수 있지만, 이에 한정되는 것은 아니다.Alkyl in the present invention means a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms. Examples of such alkyl include, but are not limited to, methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl, hexyl and the like.

본 발명에서의 알케닐은 탄소-탄소 이중 결합을 1개 이상 가진, 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알케닐의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등을 들 수 있지만, 이에 한정되는 것은 아니다.Alkenyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon double bond. Examples of such alkenyl include, but are not limited to, vinyl, allyl, isopropenyl, 2-butenyl, and the like.

본 발명에서의 알키닐은 탄소-탄소 삼중 결합을 1개 이상 가진, 탄소수 2 내지 40의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기를 의미한다. 이러한 알키닐의 예로는 에타인일(ethynyl), 2-프로파인일(2-propynyl) 등을 들 수 있지만, 이에 한정되는 것은 아니다.Alkynyl in the present invention means a monovalent substituent derived from a straight or branched chain unsaturated hydrocarbon having 2 to 40 carbon atoms having at least one carbon-carbon triple bond. Examples of such alkynyl include, but are not limited to, ethynyl, 2-propynyl, and the like.

본 발명에서의 아릴은 단독 고리 또는 2 이상의 고리가 조합된, 탄소수 6 내지 60의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 2 이상의 고리가 서로 단순 부착되거나 축합된 형태도 포함할 수 있다. 이러한 아릴의 예로, 페닐, 나프틸, 페난트릴, 안트릴 등을 들 수 있지만, 이에 한정되는 것은 아니다.Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms, a single ring or a combination of two or more rings, and may also include a form in which two or more rings are simply attached or condensed with each other. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, and the like.

본 발명에서의 헤테로아릴은 핵원자수(탄소를 포함하는 원자의 수) 5 내지 40의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로원자로 치환된다. 헤테로아릴은 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합된(fused) 형태로 부착될 수 있고, 아릴기와의 축합된 형태도 포함하는 것으로 해석할 수 있다. 이러한 헤테로아릴의 예로, 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6원 모노사이클릭 고리; 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리; 및 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등을 들 수 있지만, 이에 한정되는 것은 아니다.Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon of 5 to 40 nuclear atoms (number of atoms including carbon), at least one carbon in the ring, Preferably one to three carbons are substituted with heteroatoms such as N, O, S or Se. Heteroaryl can be interpreted that two or more rings may be attached in a simple or fused form with each other, and also include a condensed form with an aryl group. Examples of such heteroaryl include six-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; And 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.

본 발명에서의 아릴옥시는 RO-로 표시되는 1가의 치환기로서, 상기 R은 탄소수 6 내지 60의 아릴이다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등을 들 수 있지만, 이에 한정되는 것은 아니다.Aryloxy in the present invention is a monovalent substituent represented by RO-, wherein R is aryl having 6 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy and the like.

본 발명에서의 알킬옥시는 R´O-로 표시되는 1가의 치환기로서, 상기 R´는 탄소수 1 내지 40의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함하는 것으로 해석할 수 있다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등을 들 수 있지만, 이에 한정되는 것은 아니다.Alkyloxy in the present invention is a monovalent substituent represented by R'O-, wherein R 'means an alkyl having 1 to 40 carbon atoms, and has a linear, branched or cyclic structure It can be interpreted as being included. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.

본 발명에서의 아릴아민은 탄소수 6 내지 60의 아릴로 치환된 아민을 의미한다.Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.

본 발명에서의 시클로알킬은 탄소수 3 내지 40의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 놀보닐(norbornyl), 아다만틴(adamantine) 등을 들 수 있지만, 이에 한정되는 것은 아니다. Cycloalkyl in the present invention means a monovalent substituent derived from a monocyclic or polycyclic non-aromatic hydrocarbon having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.

본 발명에서의 헤테로시클로알킬은 핵원자수 3 내지 40의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O 또는 S와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등을 들 수 있지만, 이에 한정되는 것은 아니다.Heterocycloalkyl in the present invention means a monovalent substituent derived from a non-aromatic hydrocarbon having 3 to 40 nuclear atoms, wherein at least one carbon in the ring, preferably 1 to 3 carbons, is N, O or S and Are substituted with the same hetero atom. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.

본 발명에서의 알킬실릴은 탄소수 1 내지 40의 알킬로 치환된 실릴이고, 아릴실릴은 탄소수 6 내지 40의 아릴로 치환된 실릴을 의미한다.Alkylsilyl in the present invention is silyl substituted with alkyl having 1 to 40 carbon atoms, arylsilyl means silyl substituted with aryl having 6 to 40 carbon atoms.

한편, 본 발명은 양극, 음극, 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함하는 것이 특징인 유기 전계 발광 소자를 제공한다.On the other hand, the present invention is an organic electroluminescent device comprising an anode, a cathode, and at least one organic layer interposed between the anode and the cathode, wherein at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device characterized in that it comprises a.

여기서, 상기 화학식 1로 표시되는 화합물을 포함하는 유기물층은 발광층인 것이 바람직하다. 이때, 화학식 1로 표시되는 화합물이 발광층일 경우, 상기 화학식 1로 표시되는 화합물은 청색, 녹색 또는 적색의 인광 호스트 재료일 수 있다.Here, the organic material layer including the compound represented by Formula 1 is preferably a light emitting layer. In this case, when the compound represented by Formula 1 is a light emitting layer, the compound represented by Formula 1 may be a blue, green or red phosphorescent host material.

이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.

본 발명은 종래의 유기 전계 발광 소자용 재료(예를 들어, 4,4-dicarbazolybiphenyl(이하, ´CBP´라 함))보다 분자량이 클 뿐만 아니라, 넓은 에너지 밴드갭을 가지면서, 정공과 전자의 결합력을 높일 수 있는 상기 화학식 1로 표시되는 화합물을 제공하는 것이 특징이다.The present invention not only has a higher molecular weight than the conventional organic electroluminescent device material (for example, 4,4-dicarbazolybiphenyl (hereinafter referred to as 'CBP')), but also has a wide energy band gap, It is a feature to provide a compound represented by the formula (1) that can increase the binding force.

구체적으로, 본 발명의 화학식 1로 표시되는 화합물은, 벤조싸이아노피리딘(benzothienopyridine) 또는 벤조퓨로피리딘(benzofuropyridine)의 말단에 헤테로환 모이어티, 바람직하게는 인돌 유도체 모이어티(moiety)가 결합(융합)되어 있다. 벤조싸이아노피리딘(benzothienopyridine) 또는 벤조퓨로피리딘(benzofuropyridine) 골격은 높은 triplet 에너지 레벨을 가지고 있기 때문에, 본 발명의 화학식 1로 표시되는 화합물을 유기 전계 발광 소자에 사용할 경우, 소자의 인광특성을 개선함과 동시에 정공 주입 능력, 정공 수송 능력, 발광효율, 구동전압 및 수명 특성 등을 향상시킬 수 있다.Specifically, the compound represented by the formula (1) of the present invention, a heterocyclic moiety, preferably an indole derivative moiety (moiety) is bonded to the end of benzothienopyridine or benzofuropyridine Fused). Since the benzothienopyridine or benzofuropyridine skeleton has a high triplet energy level, when the compound represented by Formula 1 of the present invention is used in an organic electroluminescent device, the phosphorescence characteristics of the device are improved. At the same time, the hole injection ability, hole transport ability, luminous efficiency, driving voltage, and lifetime characteristics can be improved.

특히, 본 발명의 화학식 1로 표시되는 화합물은 벤조싸이아노피리딘 또는 벤조퓨로피리딘 골격의 말단에 결합된 인돌 유도체 모이어티로 인해 넓은 밴드갭(sky blue ~ red)을 가지면서, 정공과 전자의 결합력을 높일 수 있기 때문에 종래의 CBP에 비해 발광층의 호스트 재료, 구체적으로는 청색, 녹색 및/또는 적색의 인광 호스트 재료로서 우수한 특성을 나타낼 수 있다.In particular, the compound represented by Formula 1 of the present invention has a wide bandgap (sky blue to red) due to the indole derivative moiety bound to the terminal of the benzocyanopyridine or benzofuropyridine skeleton, Since the bonding force can be increased, it can exhibit excellent properties as a host material of the light emitting layer, specifically, a blue, green and / or red phosphorescent host material, compared to the conventional CBP.

또한, 본 발명의 화학식 1로 표시되는 화합물은 다양한 치환기(R1 내지 R3 및 Ar1)가 결합되어 화합물의 분자량이 유의적으로 증대되기 때문에 높은 유리전이온도를 나타내며, 이로 인해 종래 CBP 보다 높은 열적 안정성을 가질 수 있다.In addition, the compound represented by the formula (1) of the present invention exhibits a high glass transition temperature because a variety of substituents (R 1 to R 3 and Ar 1 ) is bonded to significantly increase the molecular weight of the compound, which is higher than the conventional CBP May have thermal stability.

본 발명의 화학식 1로 표시되는 화합물에 있어서, Y1 내지 Y4 중 축합 고리를 형성하지 않는 부분은 N을 하나 이상 포함하는 것이 바람직하다. 또한, X1 내지 X4는 모두 CR1이거나 N을 하나 이상 포함하는 것이 바람직하며, Z1 내지 Z4도 모두 CR3이거나 N을 하나 이상 포함한 것이 바람직하다.In the compound represented by the formula (1) of the present invention, the portion of the Y 1 to Y 4 that does not form a condensed ring preferably contains one or more N. In addition, it is preferable that all of X 1 to X 4 are CR 1 or include one or more N, and all of Z 1 to Z 4 are preferably CR 3 or one or more N.

한편, 본 발명의 화학식 1로 표시되는 화합물에서, 인돌 유도체 모이어티에 치환되는 Ar1은 C6~C40의 아릴기 또는 핵원자수 5 내지 40의 헤테로아릴기인 것이 바람직하다.On the other hand, in the compound represented by the formula (1) of the present invention, Ar 1 substituted in the indole derivative moiety is preferably a C 6 ~ C 40 aryl group or a heteroaryl group of 5 to 40 nuclear atoms.

여기서, 상기 Ar1의 아릴기 또는 헤테로아릴기는 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, (C6~C40의 아릴)C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 복수개의 치환기를 가질 경우, 각각의 치환기는 동일하거나 상이할 수 있다.Here, the aryl group or heteroaryl group of Ar 1 Deuterium, halogen, cyano group, C 1 ~ C 40 Alkyl group, C 2 ~ C 40 Alkenyl group, C 2 ~ C 40 Alkynyl group, C 6 ~ C 40 the aryl group, the number of nuclear atoms of 5 to 40 heteroaryl group, C 6 ~ C 40 aryloxy group, alkyloxy group of C 1 ~ C 40 of, C 6 ~ C 40 aryl amine group, a (C 6 ~ C 40 aryl) C 1 to C 40 alkyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 1 to C 40 alkylsilyl group and C 6 to C 40 arylsilyl It may be substituted with one or more substituents selected from the group consisting of groups, and when having a plurality of substituents, each substituent may be the same or different.

이러한 본 발명의 화학식 1로 표시되는 화합물의 치환체(작용기)인 R1 내지 R3 및 Ar1의 예로 하기와 같은 예(S1~S138)를 들 수 있지만, 이에 한정되는 것은 아니다.Examples of R 1 to R 3 and Ar 1 which are substituents (functional groups) of the compound represented by Formula 1 of the present invention include the following examples (S1 to S138), but are not limited thereto.

Figure PCTKR2013003806-appb-I000003
Figure PCTKR2013003806-appb-I000003

Figure PCTKR2013003806-appb-I000004
Figure PCTKR2013003806-appb-I000004

Figure PCTKR2013003806-appb-I000005
Figure PCTKR2013003806-appb-I000005

본 발명의 화학식 1로 표시되는 화합물의 치환체(작용기) 중 Ar1은, 하기 S-1 내지 S-39로 표시되는 구조로 이루어진 군에서 선택되는 것이 바람직하다.Ar 1 in the substituent (functional group) of the compound represented by Formula 1 of the present invention is preferably selected from the group consisting of structures represented by S-1 to S-39.

Figure PCTKR2013003806-appb-I000006
Figure PCTKR2013003806-appb-I000006

상기한 본 발명의 화학식 1로 표시되는 화합물은 하기 화학식 3 내지 8로 표시되는 화합물로 이루어진 군에서 선택되는 것이 바람직하나, 이에 한정되는 것은 아니다.The compound represented by Chemical Formula 1 of the present invention is preferably selected from the group consisting of compounds represented by the following Chemical Formulas 3 to 8, but is not limited thereto.

[화학식 3][Formula 3]

Figure PCTKR2013003806-appb-I000007
Figure PCTKR2013003806-appb-I000007

[화학식 4][Formula 4]

Figure PCTKR2013003806-appb-I000008
Figure PCTKR2013003806-appb-I000008

[화학식 5][Formula 5]

Figure PCTKR2013003806-appb-I000009
Figure PCTKR2013003806-appb-I000009

[화학식 6][Formula 6]

Figure PCTKR2013003806-appb-I000010
Figure PCTKR2013003806-appb-I000010

[화학식 7][Formula 7]

Figure PCTKR2013003806-appb-I000011
Figure PCTKR2013003806-appb-I000011

[화학식 8][Formula 8]

Figure PCTKR2013003806-appb-I000012
Figure PCTKR2013003806-appb-I000012

상기 화학식 3 내지 8에서, A, X1 내지 X4, Y1 내지 Y4, Z1 내지 Z4 및 Ar1는 상기 화학식 1에서 정의한 바와 동일하다.In Formulas 3 to 8, A, X 1 to X 4 , Y 1 to Y 4, Z 1 to Z 4, and Ar 1 are the same as defined in Formula 1 above.

이러한 본 발명의 화학식 1로 표시되는 화합물은 보다 구체적으로, 하기 화학식 C1 내지 C18로 표시되는 화합물로 이루어진 군에서 선택되는 것이 바람직하나, 이에 한정되는 것은 아니다.More specifically, the compound represented by Formula 1 of the present invention is preferably selected from the group consisting of compounds represented by the following Formulas C1 to C18, but is not limited thereto.

Figure PCTKR2013003806-appb-I000013
Figure PCTKR2013003806-appb-I000013

상기 화학식 C1 내지 C18에서, A, X1 내지 X4, Z1 내지 Z4 및 Ar1은 상기 화학식 1에서 정의한 바와 동일하다. 상기 화학식 C1 내지 C18로 표시되는 화합물에서 A는 S인 것이 더욱 바람직하다.In Formulas C1 to C18, A, X 1 to X 4, Z 1 to Z 4 and Ar 1 are the same as defined in Formula 1. In the compounds represented by Formulas C1 to C18, A is more preferably S.

본 발명의 화학식 1로 표시되는 화합물의 구체적인 예로 하기 화합물들(C-1 내지 C-578)을 들 수 있지만, 이에 한정되는 것은 아니다.Specific examples of the compound represented by Formula 1 of the present invention include the following compounds (C-1 to C-578), but is not limited thereto.

Figure PCTKR2013003806-appb-I000014
Figure PCTKR2013003806-appb-I000014

Figure PCTKR2013003806-appb-I000015
Figure PCTKR2013003806-appb-I000015

Figure PCTKR2013003806-appb-I000016
Figure PCTKR2013003806-appb-I000016

Figure PCTKR2013003806-appb-I000017
Figure PCTKR2013003806-appb-I000017

Figure PCTKR2013003806-appb-I000018
Figure PCTKR2013003806-appb-I000018

Figure PCTKR2013003806-appb-I000019
Figure PCTKR2013003806-appb-I000019

Figure PCTKR2013003806-appb-I000020
Figure PCTKR2013003806-appb-I000020

Figure PCTKR2013003806-appb-I000021
Figure PCTKR2013003806-appb-I000021

Figure PCTKR2013003806-appb-I000022
Figure PCTKR2013003806-appb-I000022

Figure PCTKR2013003806-appb-I000023
Figure PCTKR2013003806-appb-I000023

Figure PCTKR2013003806-appb-I000024
Figure PCTKR2013003806-appb-I000024

Figure PCTKR2013003806-appb-I000025
Figure PCTKR2013003806-appb-I000025

Figure PCTKR2013003806-appb-I000026
Figure PCTKR2013003806-appb-I000026

Figure PCTKR2013003806-appb-I000027
Figure PCTKR2013003806-appb-I000027

Figure PCTKR2013003806-appb-I000028
Figure PCTKR2013003806-appb-I000028

Figure PCTKR2013003806-appb-I000029
Figure PCTKR2013003806-appb-I000029

Figure PCTKR2013003806-appb-I000030
Figure PCTKR2013003806-appb-I000030

Figure PCTKR2013003806-appb-I000031
Figure PCTKR2013003806-appb-I000031

Figure PCTKR2013003806-appb-I000032
Figure PCTKR2013003806-appb-I000032

Figure PCTKR2013003806-appb-I000033
Figure PCTKR2013003806-appb-I000033

Figure PCTKR2013003806-appb-I000034
Figure PCTKR2013003806-appb-I000034

이와 같은 본 발명의 화학식 1로 표시되는 화합물은 하기 실시예의 합성과정을 참고하여 다양하게 합성할 수 있다.Such a compound represented by Formula 1 of the present invention can be synthesized in various ways with reference to the synthesis process of the following examples.

2. 유기 전계 발광 소자2. Organic electroluminescent device

본 발명은 상기 화학식 1로 표시되는 화합물, 바람직하게는 화학식 3 내지 8로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.The present invention provides an organic electroluminescent device comprising a compound represented by Chemical Formula 1, preferably a compound represented by Chemical Formulas 3 to 8.

본 발명은 양극(anode), 음극(cathode) 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, 상기 1층 이상의 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물, 바람직하게는 화학식 3 내지 8로 표시되는 화합물을 포함한다. 이때, 상기 화학식 3 내지 8로 표시되는 화합물은 단독으로 또는 2 이상이 혼합되어 사용될 수 있다.The present invention provides an organic electroluminescent device comprising an anode, a cathode and one or more organic material layers interposed between the anode and the cathode, wherein at least one of the one or more organic material layers is represented by Formula 1 above. The compound represented, Preferably the compound represented by Formula 3-8 is included. In this case, the compounds represented by Formulas 3 to 8 may be used alone or in combination of two or more.

상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 중 어느 하나 이상일 수 있고, 바람직하게는 정공 주입층, 정공수송층, 발광층 또는 전자수송층일 수 있고, 보다 바람직하게는 발광층일 수 있다.The one or more organic material layers may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, preferably a hole injection layer, a hole transport layer, a light emitting layer or an electron transport layer, more preferably It may be a light emitting layer.

본 발명에 따른 유기 전계 발광 소자는 발광층에 호스트 재료를 포함할 수 있는데, 이때 호스트 재료로서 상기 화학식 1로 표시되는 화합물을 사용할 수 있다. 상기 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 발광층, 바람직하게는 발광층의 청색, 녹색 또는 적색의 인광 호스트 재료로 사용할 경우, 발광층에서 정공과 전자의 결합력이 높아지기 때문에, 유기 전계 발광 소자의 효율(발광효율 및 전력효율), 수명, 휘도 및 구동전압 등이 향상될 수 있다.The organic electroluminescent device according to the present invention may include a host material in the light emitting layer. In this case, the compound represented by Formula 1 may be used as the host material. When the compound represented by Chemical Formula 1 is used as a light emitting layer of the organic EL device, preferably a blue, green or red phosphorescent host material of the light emitting layer, the binding force between the holes and the electrons in the light emitting layer is increased, so that the efficiency of the organic EL device is increased. (Luminescence efficiency and power efficiency), lifetime, brightness and driving voltage can be improved.

이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으나, 비제한적인 예로 기판, 양극, 정공주입층, 정공수송층, 발광층, 전자수송층 및 음극이 순차적으로 적층된 구조로 이루어질 수 있다. 여기서, 전자수송층 위에는 전자주입층이 추가로 적층될 수도 있다. 또한, 본 발명에 따른 유기 전계 발광 소자는 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층된 구조뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조로 이루어질 수도 있다.The structure of the organic electroluminescent device of the present invention is not particularly limited, but may be formed of a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and a cathode are sequentially stacked. Here, the electron injection layer may be further stacked on the electron transport layer. In addition, the organic electroluminescent device according to the present invention may not only have a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked, but also a structure in which an insulating layer or an adhesive layer is inserted at an interface between the electrode and the organic material layer.

한편, 본 발명에 따른 유기 전계 발광 소자에 포함되는 양극으로 사용 가능한 물질은 특별히 한정되지 않으나, 비제한적인 예로 바나듐, 크롬, 구리, 아연, 금과 같은 금속 또는 이들의 합금; 아연산화물, 인듐산화물, 인듐 주석 산화물(ITO), 인듐 아연 산화물(IZO)과 같은 금속 산화물; ZnO:Al 또는 SnO2:Sb와 같은 금속과 산화물의 조합; 폴리티오펜, 폴리(3-메틸티오펜), 폴리[3,4-(에틸렌-1,2-디옥시)티오펜](PEDT), 폴리피롤 또는 폴리아닐린과 같은 전도성 고분자; 및 카본블랙 등을 사용할 수 있다.On the other hand, the material that can be used as the anode included in the organic electroluminescent device according to the present invention is not particularly limited, but non-limiting examples include metals such as vanadium, chromium, copper, zinc, gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black and the like can be used.

본 발명에 따른 유기 전계 발광 소자에 포함되는 음극으로 사용 가능한 물질은 특별히 한정되지 않으나, 비제한적인 예로 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; 및 LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등을 사용할 수 있다.The material usable as the negative electrode included in the organic electroluminescent device according to the present invention is not particularly limited, but non-limiting examples include magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, Or metals such as lead or alloys thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.

본 발명에 따른 유기 전계 발광 소자에 포함되는 유기물층은 상기 화학식 1로 표시되는 화합물을 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 중 어느 하나에 사용하는 것을 제외하고는 당업계에 공지된 물질로 이루어질 수 있다.The organic material layer included in the organic electroluminescent device according to the present invention is known in the art except for using the compound represented by Formula 1 in any one of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer It can be made of a material.

본 발명에 따른 유기 전계 발광 소자에 포함되는 기판으로 사용 가능한 물질은 특별히 한정되지 않으나, 비제한적인 예로 실리콘 웨이퍼, 석영, 유리판, 금속판, 플라스틱 필름 및 시트 등이 사용될 수 있다. The material usable as the substrate included in the organic electroluminescent device according to the present invention is not particularly limited, but non-limiting examples may include silicon wafers, quartz, glass plates, metal plates, plastic films and sheets.

이와 같은 본 발명의 유기 전계 발광 소자는 당업계에 공지된 방법으로 제조될 수 있으며, 유기물층에 포함되는 발광층은 진공 증착법이나 용액 도포법으로 제조될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이들에 한정되지 않는다.Such an organic electroluminescent device of the present invention may be manufactured by a method known in the art, the light emitting layer included in the organic material layer may be manufactured by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.

이하 본 발명을 실시예를 통하여 상세히 설명하면 다음과 같다. 단, 하기 실시예는 본 발명을 예시하는 것일 뿐 본 발명이 하기 실시예에 의해 한정되는 것은 아니다.Hereinafter, the present invention will be described in detail with reference to the following Examples. However, the following examples are merely to illustrate the present invention and the present invention is not limited by the following examples.

[준비예 1] CORE-1의 합성Preparation Example 1 Synthesis of CORE-1

<단계 1> CORE1-A의 합성Step 1 Synthesis of CORE1-A

Figure PCTKR2013003806-appb-I000035
Figure PCTKR2013003806-appb-I000035

질소 기류 하에서 10.6g (40.13mmol)의 CORE1-A-1, 8.0g (48.15mmol)의 2-nitrophenylboronic acid, 4.8g (120.4mmol)의 NaOH과 200ml/50ml의 THF/H2O를 넣고 교반하였다. 40℃에서 1.39g (1.2mmol)의 Pd(PPh3)4를 넣고 80℃에서 12시간 동안 환류 교반하였다. 반응 종결 후 디클로로메탄으로 추출하고 유기층을 MgSO4로 건조 후 감압여과하였다. 여과된 유기층을 감압증류 한 뒤 컬럼 크로마토그래피를 이용하여 CORE1-A 6.4 g (yield: 52%)을 획득하였다. 10.6 g (40.13 mmol) of CORE1-A-1, 8.0 g (48.15 mmol) of 2-nitrophenylboronic acid, 4.8 g (120.4 mmol) of NaOH and 200 ml / 50 ml of THF / H 2 O were added and stirred under a nitrogen stream. . 1.39 g (1.2 mmol) of Pd (PPh 3 ) 4 was added at 40 ° C., and the mixture was stirred under reflux at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and the organic layer was dried over MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure and then column chromatography was used to obtain 6.4 g (yield: 52%) of CORE1-A.

1H-NMR : δ 7.59 (m, 3H), 8.00 (m, 5H), 8.21 (d, 1H), 8.50 (d, 1H), 1 H-NMR: δ 7.59 (m, 3H), 8.00 (m, 5H), 8.21 (d, 1H), 8.50 (d, 1H),

<단계 2> CORE-1의 합성<Step 2> Synthesis of CORE-1

Figure PCTKR2013003806-appb-I000036
Figure PCTKR2013003806-appb-I000036

질소 기류 하에서 CORE1-A 6.4g (20.89mmol)과 triphenylphosphine 13.7g (52.22mmol), 1,2-dichlorobenzene 100ml를 넣은 후 12시간 교반하였다. 반응 종료 후 디스틸레이션을 통해 1,2-dichlorobenzene를 제거하고 디클로로메탄으로 추출하였다. 추출된 유기층은 MgSO4로 건조 후 감압여과하였다. 여과된 유기층을 감압증류한 뒤 컬럼크로마토그래피를 이용하여 CORE-1 3.3g (yield : 57%)을 획득하였다.Under nitrogen stream, 6.4 g (20.89 mmol) of CORE1-A, 13.7 g (52.22 mmol) of triphenylphosphine, and 100 ml of 1,2-dichlorobenzene were added thereto, followed by stirring for 12 hours. After completion of the reaction, 1,2-dichlorobenzene was removed by distillation and extracted with dichloromethane. The extracted organic layer was dried over MgSO 4 and filtered under reduced pressure. The filtered organic layer was distilled under reduced pressure, and then 3.3 g (yield: 57%) of CORE-1 was obtained using column chromatography.

1H-NMR : δ 7.31 (t, 1H), 7.55 (m, 4H), 8.05 (m, 3H), 8.82 (s, 1H), 10.51 (s, 1H) 1 H-NMR: δ 7.31 (t, 1H), 7.55 (m, 4H), 8.05 (m, 3H), 8.82 (s, 1H), 10.51 (s, 1H)

[준비예 2] CORE-2 의 합성 Preparation Example 2 Synthesis of CORE-2

<단계 1> 2,5-dichloro-3-(2-chlorophenyl)pyrazine의 합성<Step 1> Synthesis of 2,5-dichloro-3- (2-chlorophenyl) pyrazine

Figure PCTKR2013003806-appb-I000037
Figure PCTKR2013003806-appb-I000037

질소 기류 하에서 28g (152.65mmol)의 2,3,5-trichloropyrazine, 23.8g (152.65mmol)의 2-chlorophenylboronic acid, 63.3g (457.9mmol)의 K2CO3와 800ml/200ml의 THF/H2O를 넣고 교반하였다. 40℃에서 5.3g (4.58mmol)의 Pd(PPh3)4를 넣고 80℃에서 12시간 동안 교반하였다. 반응 종결 후 디클로로메탄으로 추출하고 유기층을 MgSO4로 건조 후 감압여과하였다. 여과된 유기층을 감압증류한 뒤 컬럼 크로마토그래피를 이용하여 목적 화합물인 2,5-dichloro-3-(2-chlorophenyl)pyrazine 12g (yield: 30%)을 획득하였다. 28 g (152.65 mmol) 2,3,5-trichloropyrazine, 23.8 g (152.65 mmol) 2-chlorophenylboronic acid, 63.3 g (457.9 mmol) K 2 CO 3 and 800 ml / 200 ml THF / H 2 O under nitrogen stream Was added and stirred. 5.3 g (4.58 mmol) of Pd (PPh 3 ) 4 was added at 40 ° C. and stirred at 80 ° C. for 12 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and the organic layer was dried over MgSO 4 and filtered under reduced pressure. After distillation under reduced pressure the filtered organic layer was purified by column chromatography to obtain 12g (yield: 30%) of the target compound 2,5-dichloro-3- (2-chlorophenyl) pyrazine.

1H-NMR : δ 7.37(m, 2H), 7.58(d, 1H), 7.75(d, 1H), 8.69(s, 1H) 1 H-NMR: δ 7.37 (m, 2H), 7.58 (d, 1H), 7.75 (d, 1H), 8.69 (s, 1H)

<단계 2> ethyl 3-(2-(3,6-dichloropyrazin-2-yl)phenylthio)propanoate의 합성<Step 2> Synthesis of ethyl 3- (2- (3,6-dichloropyrazin-2-yl) phenylthio) propanoate

Figure PCTKR2013003806-appb-I000038
Figure PCTKR2013003806-appb-I000038

질소 기류 하에서 12g (46.2mmol)의 2,5-dichloro-3-(2-chlorophenyl)pyrazine, 12.4g (92.47mmol)의 ethyl 3-mercaptopropanoate, 2.96g (3.23mmol)의 Pd2dba3, 0.1g (0.7mmol)의 dpephos, 16g (115.6mmol)의 K2CO3를 250ml의 Toluene에 넣고 110℃에서 15시간 교반하였다. 반응 종결 후 디클로로메탄으로 추출하고 유기층을 MgSO4로 건조 후 감압여과하였다. 여과된 유기층을 감압증류한 뒤 컬럼 크로마토그래피를 이용하여 ethyl 3-(2-(3,6-dichloropyrazin-2-yl)phenylthio)propanoate 14.7g (yield: 89%)을 획득하였다.12 g (46.2 mmol) of 2,5-dichloro-3- (2-chlorophenyl) pyrazine under nitrogen stream, 12.4 g (92.47 mmol) of ethyl 3-mercaptopropanoate, 2.96 g (3.23 mmol) of Pd 2 dba 3 , 0.1 g (0.7 mmol) of dpephos and 16 g (115.6 mmol) of K 2 CO 3 were added to 250 ml of toluene and stirred at 110 ° C. for 15 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and the organic layer was dried over MgSO 4 and filtered under reduced pressure. After distillation under reduced pressure the filtered organic layer was purified by column chromatography to give 14.7g (yield: 89%) of ethyl 3- (2- (3,6-dichloropyrazin-2-yl) phenylthio) propanoate.

1H-NMR : δ 1.27 (m, 3H), 2.52 (m, 2H), 3.03 (m, 2H), 4.09 (m, 2H), 7.30 (m, 2H), 7.71 (d, 1H), 7.87 (d, 1H), 8.69 (s, 1H) 1 H-NMR: δ 1.27 (m, 3H), 2.52 (m, 2H), 3.03 (m, 2H), 4.09 (m, 2H), 7.30 (m, 2H), 7.71 (d, 1H), 7.87 ( d, 1 H), 8.69 (s, 1 H)

<단계 3> CORE2-A 의 합성Step 3 Synthesis of CORE2-A

Figure PCTKR2013003806-appb-I000039
Figure PCTKR2013003806-appb-I000039

질소 기류 하에서 14.7g (41.1mmol)의 ethyl 3-(2-(3,6-dichloropyrazin-2-yl)phenylthio)propanoate, 6.92g (61.7mmol)의 potassium tert-butoxide를 200ml의 THF에 넣고 50℃에서 8시간 교반하였다. 반응 종결 후 디클로로메탄으로 추출하고 유기층을 MgSO4로 건조 후 감압여과하였다. 여과된 유기층을 감압증류한 뒤 컬럼 크로마토그래피를 이용하여 목적 화합물인 CORE2-A 6.6g (yield: 80%)을 획득하였다. Under nitrogen stream, 14.7 g (41.1 mmol) of ethyl 3- (2- (3,6-dichloropyrazin-2-yl) phenylthio) propanoate and 6.92 g (61.7 mmol) of potassium tert-butoxide were added to 200 ml of THF. Stirred for 8 hours. After completion of the reaction, the mixture was extracted with dichloromethane, and the organic layer was dried over MgSO 4 and filtered under reduced pressure. After distilling under reduced pressure on the filtered organic layer, 6.6 g (yield: 80%) of the target compound, CORE2-A, was obtained by column chromatography.

1H-NMR : δ 7.51(m, 2H), 8.02(m, 2H), 8.87(s, 1H) 1 H-NMR: δ 7.51 (m, 2H), 8.02 (m, 2H), 8.87 (s, 1H)

<단계 4> CORE2-B의 합성Step 4 Synthesis of CORE2-B

Figure PCTKR2013003806-appb-I000040
Figure PCTKR2013003806-appb-I000040

CORE1-A-1 대신 CORE2-A 을 사용하는 것을 제외하고는 준비예 1의 <단계 1>과 동일한 과정을 수행하여 CORE2-B 6g (yield: 67%)을 획득하였다.A CORE2-B 6g (yield: 67%) was obtained in the same manner as in <Step 1> of Preparation Example 1, except that CORE2-A was used instead of CORE1-A-1.

1H-NMR : δ 7.61(m, 3H), 8.02(m, 4H), 8.18(d, 1H) 1 H-NMR: δ 7.61 (m, 3H), 8.02 (m, 4H), 8.18 (d, 1H)

<단계 5> CORE-2 의 합성Step 5 Synthesis of CORE-2

Figure PCTKR2013003806-appb-I000041
Figure PCTKR2013003806-appb-I000041

CORE1-A 대신 CORE2-B를 사용하는 것을 제외하고는 준비예 1의 <단계 2>와 동일한 과정을 수행하여 CORE-2 3.2g(yield: 54%)을 얻었다.Except for using CORE2-B instead of CORE1-A was carried out the same procedure as in <Step 2> of Preparation Example 1 to obtain 3.2g (yield: 54%) of CORE-2.

1H-NMR : δ 7.27(t, 1H), 7.59(m, 4H), 8.07(m, 3H) 10.50(s, 1H) 1 H-NMR: δ 7.27 (t, 1H), 7.59 (m, 4H), 8.07 (m, 3H) 10.50 (s, 1H)

[준비예 3] CORE-3A 및 3B의 합성 Preparation Example 3 Synthesis of CORE-3A and 3B

<단계 1> 2,5-dichloro-3-(2-chlorophenyl)pyridine의 합성<Step 1> Synthesis of 2,5-dichloro-3- (2-chlorophenyl) pyridine

Figure PCTKR2013003806-appb-I000042
Figure PCTKR2013003806-appb-I000042

2,3,5-trichloropyrazine 대신 2,3,5-trichloropyridine을 사용하는 것을 제외하고는 준비예 2의 <단계 1>과 동일한 과정을 수행하여 2,5-dichloro-3-(2-chlorophenyl)pyridine 13g (yield: 46%)을 획득하였다.2,5-dichloro-3- (2-chlorophenyl) pyridine by following the same procedure as in <Step 1> of Preparation Example 2, except that 2,3,5-trichloropyridine was used instead of 2,3,5-trichloropyrazine. 13g (yield: 46%) was obtained.

1H-NMR : δ 7.38 (m, 2H), 7.75 (m, 2H), 8.81 (s, 1H) 1 H-NMR: δ 7.38 (m, 2H), 7.75 (m, 2H), 8.81 (s, 1H)

<단계2> ethyl 3-(2-(2,5-dichloropyridin-3-yl)phenylthio)propanoate의 합성<Step 2> Synthesis of ethyl 3- (2- (2,5-dichloropyridin-3-yl) phenylthio) propanoate

Figure PCTKR2013003806-appb-I000043
Figure PCTKR2013003806-appb-I000043

2,5-dichloro-3-(2-chlorophenyl)pyrazine 대신 2,5-dichloro-3-(2-chlorophenyl)pyridine을 사용하는 것을 제외하고는 준비예 2의 <단계 2>와 동일한 과정을 수행하여 ethyl 3-(2-(2,5-dichloropyridin-3-yl)phenylthio)propanoate 15.3g (yield: 85%)을 획득하였다.Except for using 2,5-dichloro-3- (2-chlorophenyl) pyridine instead of 2,5-dichloro-3- (2-chlorophenyl) pyrazine, the same procedure as in <Step 2> of Preparation Example 2 was performed. 15.3 g (yield: 85%) of ethyl 3- (2- (2,5-dichloropyridin-3-yl) phenylthio) propanoate was obtained.

1H-NMR : δ 1.28 (m, 3H), 2.56 (m, 2H), 3.32 (m, 2H), 4.19 (m, 2H), 7.39 (m, 2H), 7.64 (m, 2H), 8.44 (s, 1H), 8.67 (s, 1H) 1 H-NMR: δ 1.28 (m, 3H), 2.56 (m, 2H), 3.32 (m, 2H), 4.19 (m, 2H), 7.39 (m, 2H), 7.64 (m, 2H), 8.44 ( s, 1 H), 8.67 (s, 1 H)

<단계3> CORE3-A의 합성<Step 3> Synthesis of CORE3-A

Figure PCTKR2013003806-appb-I000044
Figure PCTKR2013003806-appb-I000044

ethyl 3-(2-(3,6-dichloropyrazin-2-yl)phenylthio)propanoate 대신 ethyl 3-(2-(2,5-dichloropyridin-3-yl)phenylthio)propanoate을 사용하는 것을 제외하고는 준비예 2의 <단계 3>과 동일한 과정을 수행하여 CORE3-A 7.4g (yield: 78%)을 획득하였다.Preparation example except for using ethyl 3- (2- (2,5-dichloropyridin-3-yl) phenylthio) propanoate instead of ethyl 3- (2- (3,6-dichloropyrazin-2-yl) phenylthio) propanoate CORE3-A 7.4 g (yield: 78%) was obtained by performing the same procedure as in <Step 3> of 2.

1H-NMR : δ 7.48 (m, 2H), 7.96 (m, 2H), 8.49 (d, 1H), 8.81 (s, 1H) 1 H-NMR: δ 7.48 (m, 2H), 7.96 (m, 2H), 8.49 (d, 1H), 8.81 (s, 1H)

<단계4> CORE3-B의 합성Step 4 Synthesis of CORE3-B

Figure PCTKR2013003806-appb-I000045
Figure PCTKR2013003806-appb-I000045

CORE1-A-1 대신 CORE3-A를 사용하는 것을 제외하고는 준비예 1의 <단계 1>과 동일한 과정을 수행하여 CORE3-B 6.2g (yield: 60%)을 획득하였다.6.2g (yield: 60%) of CORE3-B was obtained by performing the same process as <Step 1> of Preparation Example 1, except that CORE3-A was used instead of CORE1-A-1.

1H-NMR : δ 7.49 (m, 2H), 7.66 (t, 1H), 8.01 (m, 4H), 8.19 (d, 1H), 8.43 (d, 1H), 9.36(s, 1H) 1 H-NMR: δ 7.49 (m, 2H), 7.66 (t, 1H), 8.01 (m, 4H), 8.19 (d, 1H), 8.43 (d, 1H), 9.36 (s, 1H)

<단계5> CORE-3A 및 3B의 합성Step 5 Synthesis of CORE-3A and 3B

Figure PCTKR2013003806-appb-I000046
Figure PCTKR2013003806-appb-I000046

CORE1-A 대신 CORE3-B 을 사용하는 것을 제외하고는 준비예 1의 <단계 2>과 동일한 과정을 수행하여 CORE-3A 1.8g(yield: 32%) CORE-3B 2.0g(yield: 36%)을 얻었다.CORE-3A 1.8g (yield: 32%) CORE-3B 2.0g (yield: 36%) by following the same procedure as in <Step 2> of Preparation Example 1, except that CORE3-B was used instead of CORE1-A. Got.

CORE-3A 1H-NMR : δ 7.32 (t, 1H), 7.49 (m, 3H), 7.81 (s, 1H), 8.05 (m, 2H), 8.49 (d, 1H), 10.35 (s, 1H)CORE-3A 1 H-NMR: δ 7.32 (t, 1H), 7.49 (m, 3H), 7.81 (s, 1H), 8.05 (m, 2H), 8.49 (d, 1H), 10.35 (s, 1H)

CORE-3B 1H-NMR : δ 7.31 (t, 1H), 7.51 (m, 3H), 7.83 (d, 1H), 8.02 (d, 1H), 8.15 (d, 1H), 8.47 (d, 1H), 9.55(s, 1H)CORE-3B 1 H-NMR: δ 7.31 (t, 1H), 7.51 (m, 3H), 7.83 (d, 1H), 8.02 (d, 1H), 8.15 (d, 1H), 8.47 (d, 1H) , 9.55 (s, 1H)

[준비예 4] CORE-4A 및 4B의 합성 Preparation Example 4 Synthesis of CORE-4A and 4B

<단계 1> 3-(2-nitrophenyl)benzofuro[2,3-b]pyridine의 합성Step 1 Synthesis of 3- (2-nitrophenyl) benzofuro [2,3-b] pyridine

Figure PCTKR2013003806-appb-I000047
Figure PCTKR2013003806-appb-I000047

CORE1-A-1 대신 3-chlorobenzofuro[2,3-b]pyridine을 사용하는 것을 제외하고는 준비예 1의 <단계 1>과 동일한 과정을 수행하여 3-(2-nitrophenyl)benzofuro[2,3-b]pyridine 9.7g (yield: 56%)을 획득하였다.Except for using 3-chlorobenzofuro [2,3-b] pyridine instead of CORE1-A-1, the same procedure as in <Step 1> of Preparation Example 1 was carried out to give 3- (2-nitrophenyl) benzofuro [2,3 -b] pyridine 9.7g (yield: 56%) was obtained.

1H-NMR : δ 7.34 (m, 2H), 7.66 (m, 2H), 7.95 (m, 4H), 8.18 (d, 1H), 9.50 (s, 1H) 1 H-NMR: δ 7.34 (m, 2H), 7.66 (m, 2H), 7.95 (m, 4H), 8.18 (d, 1H), 9.50 (s, 1H)

<단계 2> CORE-4A 및 4B의 합성Step 2 Synthesis of CORE-4A and 4B

Figure PCTKR2013003806-appb-I000048
Figure PCTKR2013003806-appb-I000048

CORE1-A 대신 3-(2-nitrophenyl)benzofuro[2,3-b]pyridine을 사용하는 것을 제외하고는 준비예 1의 <단계 2>와 동일한 과정을 수행하여 CORE-4A 2.8g(yield: 32%), CORE-4B 3.0g (yield: 35%)을 얻었다.Except for using 3- (2-nitrophenyl) benzofuro [2,3-b] pyridine instead of CORE1-A, the same procedure as in <Step 2> of Preparation Example 1 was performed to obtain 2.8 g of CORE-4A (yield: 32). %), CORE-4B 3.0g (yield: 35%) was obtained.

CORE-4A 1H-NMR : δ 7.34 (m, 3H), 7.50 (t, 1H), 7.65 (m, 2H), 7.80 (s, 1H), 7.92 (d, 1H), 8.15(d, 1H), 10.45(s, 1H)CORE-4A 1 H-NMR: δ 7.34 (m, 3H), 7.50 (t, 1H), 7.65 (m, 2H), 7.80 (s, 1H), 7.92 (d, 1H), 8.15 (d, 1H) , 10.45 (s, 1H)

CORE-4B 1H-NMR : δ 7.32 (m, 3H), 7.49 (t, 1H), 7.64 (m, 2H), 7.89 (d, 1H), 8.13 (d, 1H), 9.53(s, 1H), 10.42(s, 1H)CORE-4B 1 H-NMR: δ 7.32 (m, 3H), 7.49 (t, 1H), 7.64 (m, 2H), 7.89 (d, 1H), 8.13 (d, 1H), 9.53 (s, 1H) , 10.42 (s, 1H)

[합성예 1] Mat-1의 합성Synthesis Example 1 Synthesis of Mat-1

Figure PCTKR2013003806-appb-I000049
Figure PCTKR2013003806-appb-I000049

질소 기류 하에서 CORE-1 (3.28g, 12.00mmol), 1-bromo-3,5-diphenylbenzene (7.39g, 24.00mmol), Cu powder(0.09g, 1.30mmol), K2CO3(3.58g, 26.00mmol), Na2SO4(3.70g, 26.00mmol) 및 nitrobenzene(100ml)를 혼합하고 190℃에서 12시간 동안 교반하였다. CORE-1 (3.28g, 12.00mmol), 1-bromo-3,5-diphenylbenzene (7.39g, 24.00mmol), Cu powder (0.09g, 1.30mmol), K 2 CO 3 (3.58g, 26.00) under nitrogen stream mmol), Na 2 SO 4 (3.70 g, 26.00 mmol) and nitrobenzene (100 ml) were mixed and stirred at 190 ° C. for 12 hours.

반응이 종결된 후 nitrobenzene을 제거하고 메틸렌클로라이드로 유기층을 분리한 다음 MgSO4를 사용하여 물을 제거하였다. 유기층의 용매를 제거한 후 컬럼크로마토그래피로 정제하여 목적 화합물인 Mat-1 (4.22g, 수율 70%)을 얻었다.After the reaction was completed, nitrobenzene was removed, the organic layer was separated with methylene chloride, and water was removed using MgSO 4 . After removing the solvent of the organic layer was purified by column chromatography to give the title compound Mat-1 (4.22g, 70% yield).

Exact Mass: 502.15g/molExact Mass: 502.15 g / mol

Elemental Analysis: C, 83.64; H, 4.41; N, 5.57; S, 6.38Elemental Analysis: C, 83.64; H, 4.41; N, 5.57; S, 6.38

[합성예 2] Mat-2의 합성Synthesis Example 2 Synthesis of Mat-2

Figure PCTKR2013003806-appb-I000050
Figure PCTKR2013003806-appb-I000050

1-bromo-3,5-diphenylbenzene 대신 2-bromo-4,6-diphenylpyridine을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Mat-2 (4.04g, 수율 67%)을 얻었다.Except for using 2-bromo-4,6-diphenylpyridine instead of 1-bromo-3,5-diphenylbenzene, the same procedure as in Synthesis Example 1 was carried out to obtain Mat-2 (4.04 g, yield 67%) as a target compound. Got it.

Exact Mass: 503.15g/molExact Mass: 503.15 g / mol

Elemental Analysis: C, 81.09; H, 4.20; N, 8.34; S, 6.37Elemental Analysis: C, 81.09; H, 4. 20; N, 8.34; S, 6.37

[합성예 3] Mat-3의 합성Synthesis Example 3 Synthesis of Mat-3

Figure PCTKR2013003806-appb-I000051
Figure PCTKR2013003806-appb-I000051

질소 기류 하에서 CORE-1 (3.28g, 12.00mmol), 2-chloro-4,6-diphenylpyrimidine (6.38g, 24.00mmol), NaH (3.45g, 14.40mmol) 및 DMF(80ml)를 혼합하고 상온에서 3시간 동안 교반하였다. 반응이 종결된 후 물을 넣고 고체 화합물을 filter한 후, 컬럼 크로마토그래피로 정제하여 목적 화합물인 Mat-3 (4.89g, 수율 81%)를 얻었다.Under nitrogen stream, mix CORE-1 (3.28g, 12.00mmol), 2-chloro-4,6-diphenylpyrimidine (6.38g, 24.00mmol), NaH (3.45g, 14.40mmol) and DMF (80ml) and add 3 at room temperature Stir for hours. After the reaction was completed, water was added, the solid compound was filtered and purified by column chromatography to obtain Mat-3 (4.89 g, yield 81%) as a target compound.

Exact Mass: 504.14g/molExact Mass: 504.14 g / mol

Elemental Analysis: C, 78.55; H, 3.99; N, 11.10; S, 6.35Elemental Analysis: C, 78.55; H, 3.99; N, 11.10; S, 6.35

[합성예 4] Mat-4의 합성Synthesis Example 4 Synthesis of Mat-4

Figure PCTKR2013003806-appb-I000052
Figure PCTKR2013003806-appb-I000052

2-chloro-4,6-diphenylpyrimidine 대신 2-chloro-4,6-diphenyl-1,3,5-triazine을 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Mat-4 4.84g, 수율 80%)을 얻었다.Except for using 2-chloro-4,6-diphenyl-1,3,5-triazine instead of 2-chloro-4,6-diphenylpyrimidine, the same procedure as in Synthesis Example 3 was carried out, thereby the target compound Mat-4 4.84 g, yield 80%) was obtained.

Exact Mass: 505g/molExact Mass: 505g / mol

Elemental Analysis: C, 76.02; H, 3.79; N, 13.85; S, 6.34Elemental Analysis: C, 76.02; H, 3.79; N, 13.85; S, 6.34

[합성예 5] Mat-5의 합성Synthesis Example 5 Synthesis of Mat-5

Figure PCTKR2013003806-appb-I000053
Figure PCTKR2013003806-appb-I000053

2-chloro-4,6-diphenylpyrimidine 대신 2,4-di(biphenyl-3-yl)-6-chloro-1,3,5-triazine을 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Mat-5 (5.99g, 수율 76%)을 얻었다.Except for using 2,4-di (biphenyl-3-yl) -6-chloro-1,3,5-triazine instead of 2-chloro-4,6-diphenylpyrimidine Mat-5 (5.99g, yield 76%) was obtained as the target compound.

Exact Mass: 657.20g/molExact Mass: 657.20 g / mol

Elemental Analysis: C, 80.34; H, 4.14; N, 10.65; S, 4.87Elemental Analysis: C, 80.34; H, 4.14; N, 10.65; S, 4.87

[합성예 6] Mat-6의 합성Synthesis Example 6 Synthesis of Mat-6

Figure PCTKR2013003806-appb-I000054
Figure PCTKR2013003806-appb-I000054

1-bromo-3,5-diphenylbenzene 대신 3-bromo-9-phenyl-9H-carbazole을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Mat-6 (4.38g, 수율 71%)을 얻었다.Except for using 3-bromo-9-phenyl-9H-carbazole instead of 1-bromo-3,5-diphenylbenzene, the same procedure as in Synthesis Example 1 was performed, thereby obtaining Mat-6 (4.38g, 71% yield). )

Exact Mass: 515.15g/molExact Mass: 515.15 g / mol

Elemental Analysis: C, 81.53; H, 4.11; N, 8.15; S, 6.22Elemental Analysis: C, 81.53; H, 4.11; N, 8. 15; S, 6.22

[합성예 7] Mat-7의 합성Synthesis Example 7 Synthesis of Mat-7

Figure PCTKR2013003806-appb-I000055
Figure PCTKR2013003806-appb-I000055

1-bromo-3,5-diphenylbenzene 대신 2-bromo-5-phenylpyridine을 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Mat-7 (3.48g, 수율 68%)을 얻었다.Except for using 2-bromo-5-phenylpyridine instead of 1-bromo-3,5-diphenylbenzene was carried out in the same manner as in Synthesis Example 1 to obtain the target compound Mat-7 (3.48g, 68% yield).

Exact Mass: 427.11g/molExact Mass: 427.11 g / mol

Elemental Analysis: C, 78.66; H, 4.01; N, 9.83; S, 7.50Elemental Analysis: C, 78.66; H, 4.01; N, 9.83; S, 7.50

[합성예 8] Mat-8의 합성Synthesis Example 8 Synthesis of Mat-8

Figure PCTKR2013003806-appb-I000056
Figure PCTKR2013003806-appb-I000056

CORE-1 대신 CORE-2를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Mat-8 (4.22g, 수율 70%)을 얻었다.Except for using CORE-2 instead of CORE-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound Mat-8 (4.22g, yield 70%).

Exact Mass: 503.15g/molExact Mass: 503.15 g / mol

Elemental Analysis: C, 81.09; H, 4.20; N, 8.34; S, 6.37Elemental Analysis: C, 81.09; H, 4. 20; N, 8.34; S, 6.37

[합성예 9] Mat-9의 합성Synthesis Example 9 Synthesis of Mat-9

Figure PCTKR2013003806-appb-I000057
Figure PCTKR2013003806-appb-I000057

CORE-1 대신 CORE-2를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 목적 화합물인 Mat-9 (3.93g, 수율 65%)을 얻었다.Except for using CORE-2 instead of CORE-1 was carried out in the same manner as in Synthesis Example 2 to obtain the target compound Mat-9 (3.93g, yield 65%).

Exact Mass: 504.14g/molExact Mass: 504.14 g / mol

Elemental Analysis: C, 78.55; H, 3.99; N, 11.10; S, 6.35Elemental Analysis: C, 78.55; H, 3.99; N, 11.10; S, 6.35

[합성예 10] Mat-10의 합성Synthesis Example 10 Synthesis of Mat-10

Figure PCTKR2013003806-appb-I000058
Figure PCTKR2013003806-appb-I000058

CORE-1 대신 CORE-2를 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Mat-10 (4.48g, 수율 74%)을 얻었다.Except for using CORE-2 instead of CORE-1 was carried out in the same manner as in Synthesis Example 3 to obtain the target compound Mat-10 (4.48g, 74% yield).

Exact Mass: 505.14g/molExact Mass: 505.14 g / mol

Elemental Analysis: C, 76.02; H, 3.79; N, 13.85; S, 6.34Elemental Analysis: C, 76.02; H, 3.79; N, 13.85; S, 6.34

[합성예 11] Mat-11의 합성Synthesis Example 11 Synthesis of Mat-11

Figure PCTKR2013003806-appb-I000059
Figure PCTKR2013003806-appb-I000059

CORE-1 대신 CORE-2를 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 Mat-11 (4.31g, 수율 71%)을 얻었다.Except for using CORE-2 instead of CORE-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound Mat-11 (4.31g, 71% yield).

Exact Mass: 506.13g/molExact Mass: 506.13 g / mol

Elemental Analysis: C, 73.50; H, 3.58; N, 16.59; S, 6.33Elemental Analysis: C, 73.50; H, 3.58; N, 16.59; S, 6.33

[합성예 12] Mat-12의 합성Synthesis Example 12 Synthesis of Mat-12

Figure PCTKR2013003806-appb-I000060
Figure PCTKR2013003806-appb-I000060

CORE-1 대신 CORE-2를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Mat-12 (5.92g, 수율 75%)을 얻었다.Except for using CORE-2 instead of CORE-1 was carried out in the same manner as in Synthesis Example 5 to obtain the target compound Mat-12 (5.92g, yield 75%).

Exact Mass: 658.19g/molExact Mass: 658.19 g / mol

Elemental Analysis: C, 78.40; H, 3.98; N, 12.76; S, 4.87Elemental Analysis: C, 78.40; H, 3.98; N, 12.76; S, 4.87

[합성예 13] Mat-13의 합성Synthesis Example 13 Synthesis of Mat-13

Figure PCTKR2013003806-appb-I000061
Figure PCTKR2013003806-appb-I000061

CORE-1 대신 CORE-2를 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 Mat-13 (4.08g, 수율 66%)을 얻었다.Except for using CORE-2 instead of CORE-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound Mat-13 (4.08g, 66% yield).

Exact Mass: 516.14g/molExact Mass: 516.14 g / mol

Elemental Analysis: C, 79.05; H, 3.90; N, 10.84; S, 6.21Elemental Analysis: C, 79.05; H, 3. 90; N, 10.84; S, 6.21

[합성예 14] Mat-14의 합성Synthesis Example 14 Synthesis of Mat-14

Figure PCTKR2013003806-appb-I000062
Figure PCTKR2013003806-appb-I000062

CORE-1 대신 CORE-2를 사용하는 것을 제외하고는 합성예 7과 동일한 과정을 수행하여 목적 화합물인 Mat-14 (3.23g, 수율 63%)을 얻었다.Except for using CORE-2 instead of CORE-1 was carried out in the same manner as in Synthesis Example 7 to obtain the target compound Mat-14 (3.23g, 63% yield).

Exact Mass: 428.11g/molExact Mass: 428.11 g / mol

Elemental Analysis: C, 75.68; H, 3.76; N, 13.07; S, 7.48Elemental Analysis: C, 75.68; H, 3.76; N, 13.07; S, 7.48

[합성예 15] Mat-15의 합성Synthesis Example 15 Synthesis of Mat-15

Figure PCTKR2013003806-appb-I000063
Figure PCTKR2013003806-appb-I000063

CORE-1 대신 CORE-3A를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Mat-15 (4.21g, 수율 70%)을 얻었다.Except for using CORE-3A instead of CORE-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound Mat-15 (4.21g, 70% yield).

Exact Mass: 502.15g/molExact Mass: 502.15 g / mol

Elemental Analysis: C, 83.64; H, 4.41; N, 5.57; S, 6.38 Elemental Analysis: C, 83.64; H, 4.41; N, 5.57; S, 6.38

[합성예 16] Mat-16의 합성Synthesis Example 16 Synthesis of Mat-16

Figure PCTKR2013003806-appb-I000064
Figure PCTKR2013003806-appb-I000064

CORE-1 대신 CORE-3A를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 목적 화합물인 Mat-16 (3.62g, 수율 60%)을 얻었다.Except for using CORE-3A instead of CORE-1 was carried out in the same manner as in Synthesis Example 2 to obtain the target compound Mat-16 (3.62g, yield 60%).

Exact Mass: 503.15g/molExact Mass: 503.15 g / mol

Elemental Analysis: C, 81.09; H, 4.20; N, 8.34; S, 6.37 Elemental Analysis: C, 81.09; H, 4. 20; N, 8.34; S, 6.37

[합성예 17] Mat-17의 합성Synthesis Example 17 Synthesis of Mat-17

Figure PCTKR2013003806-appb-I000065
Figure PCTKR2013003806-appb-I000065

CORE-1 대신 CORE-3A를 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Mat-17 (4.53g, 수율 75%)을 얻었다.Except for using CORE-3A instead of CORE-1 was carried out in the same manner as in Synthesis Example 3 to obtain the target compound Mat-17 (4.53g, yield 75%).

Exact Mass: 504.14g/molExact Mass: 504.14 g / mol

Elemental Analysis: C, 78.55; H, 3.99; N, 11.10; S, 6.35 Elemental Analysis: C, 78.55; H, 3.99; N, 11.10; S, 6.35

[합성예 18] Mat-18의 합성Synthesis Example 18 Synthesis of Mat-18

Figure PCTKR2013003806-appb-I000066
Figure PCTKR2013003806-appb-I000066

CORE-1 대신 CORE-3A를 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 Mat-18 (4.36g, 수율 72%)을 얻었다.Except for using CORE-3A instead of CORE-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound Mat-18 (4.36g, 72% yield).

Exact Mass: 505.14g/molExact Mass: 505.14 g / mol

Elemental Analysis: C, 76.02; H, 3.79; N, 13.85; S, 6.34 Elemental Analysis: C, 76.02; H, 3.79; N, 13.85; S, 6.34

[합성예 19] Mat-19의 합성Synthesis Example 19 Synthesis of Mat-19

Figure PCTKR2013003806-appb-I000067
Figure PCTKR2013003806-appb-I000067

CORE-1 대신 CORE-3A를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Mat-19 (5.51g, 수율 70%)을 얻었다.Except for using CORE-3A instead of CORE-1 was carried out in the same manner as in Synthesis Example 5 to obtain the target compound Mat-19 (5.51g, yield 70%).

Exact Mass: 657.20 g/molExact Mass: 657.20 g / mol

Elemental Analysis: C, 80.34; H, 4.14; N, 10.65; S, 4.87 Elemental Analysis: C, 80.34; H, 4.14; N, 10.65; S, 4.87

[합성예 20] Mat-20의 합성Synthesis Example 20 Synthesis of Mat-20

Figure PCTKR2013003806-appb-I000068
Figure PCTKR2013003806-appb-I000068

CORE-1 대신 CORE-3A를 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 Mat-20 (3.98g, 수율 63%)을 얻었다.Except for using CORE-3A instead of CORE-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound Mat-20 (3.98g, 63% yield).

Exact Mass: 515.15g/molExact Mass: 515.15 g / mol

Elemental Analysis: C, 81.53; H, 4.11; N, 8.15; S, 6.22 Elemental Analysis: C, 81.53; H, 4.11; N, 8. 15; S, 6.22

[합성예 21] Mat-21의 합성Synthesis Example 21 Synthesis of Mat-21

Figure PCTKR2013003806-appb-I000069
Figure PCTKR2013003806-appb-I000069

CORE-1 대신 CORE-3A를 사용하는 것을 제외하고는 합성예 7과 동일한 과정을 수행하여 목적 화합물인 Mat-21 (3.33g, 수율 65%)을 얻었다.Except for using CORE-3A instead of CORE-1 was carried out in the same manner as in Synthesis Example 7 to obtain the target compound Mat-21 (3.33g, 65% yield).

Exact Mass: 427.11g/molExact Mass: 427.11 g / mol

Elemental Analysis: C, 78.66; H, 4.01; N, 9.83; S, 7.50 Elemental Analysis: C, 78.66; H, 4.01; N, 9.83; S, 7.50

[합성예 22] Mat-22의 합성Synthesis Example 22 Synthesis of Mat-22

Figure PCTKR2013003806-appb-I000070
Figure PCTKR2013003806-appb-I000070

CORE-1 대신 CORE-3B를 사용하는 것을 제외하고는 합성예 1과 동일한 과정을 수행하여 목적 화합물인 Mat-22 (4.33g, 수율 72%)을 얻었다.Except for using CORE-3B instead of CORE-1 was carried out in the same manner as in Synthesis Example 1 to obtain the target compound Mat-22 (4.33g, 72% yield).

Exact Mass: 502.15g/molExact Mass: 502.15 g / mol

Elemental Analysis: C, 83.64; H, 4.41; N, 5.57; S, 6.38 Elemental Analysis: C, 83.64; H, 4.41; N, 5.57; S, 6.38

[합성예 23] Mat-23의 합성Synthesis Example 23 Synthesis of Mat-23

Figure PCTKR2013003806-appb-I000071
Figure PCTKR2013003806-appb-I000071

CORE-1 대신 CORE-3B를 사용하는 것을 제외하고는 합성예 2와 동일한 과정을 수행하여 목적 화합물인 Mat-23 (3.92g, 수율 65%)을 얻었다.Except for using CORE-3B instead of CORE-1 was carried out in the same manner as in Synthesis Example 2 to obtain the target compound Mat-23 (3.92g, 65% yield).

Exact Mass: 503.15g/molExact Mass: 503.15 g / mol

Elemental Analysis: C, 81.09; H, 4.20; N, 8.34; S, 6.37 Elemental Analysis: C, 81.09; H, 4. 20; N, 8.34; S, 6.37

[합성예 24] Mat-24의 합성Synthesis Example 24 Synthesis of Mat-24

Figure PCTKR2013003806-appb-I000072
Figure PCTKR2013003806-appb-I000072

CORE-1 대신 CORE-3B를 사용하는 것을 제외하고는 합성예 3과 동일한 과정을 수행하여 목적 화합물인 Mat-24 (4.23g, 수율 70%)을 얻었다.Except for using CORE-3B instead of CORE-1 was carried out in the same manner as in Synthesis Example 3 to obtain the target compound Mat-24 (4.23g, 70% yield).

Exact Mass: 504.14g/molExact Mass: 504.14 g / mol

Elemental Analysis: C, 78.55; H, 3.99; N, 11.10; S, 6.35 Elemental Analysis: C, 78.55; H, 3.99; N, 11.10; S, 6.35

[합성예 25] Mat-25의 합성Synthesis Example 25 Synthesis of Mat-25

Figure PCTKR2013003806-appb-I000073
Figure PCTKR2013003806-appb-I000073

CORE-1 대신 CORE-3B를 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 Mat-25 (4.24g, 수율 70%)을 얻었다.Except for using CORE-3B instead of CORE-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound Mat-25 (4.24g, 70% yield).

Exact Mass: 505.14g/molExact Mass: 505.14 g / mol

Elemental Analysis: C, 76.02; H, 3.79; N, 13.85; S, 6.34 Elemental Analysis: C, 76.02; H, 3.79; N, 13.85; S, 6.34

[합성예 26] Mat-26의 합성Synthesis Example 26 Synthesis of Mat-26

Figure PCTKR2013003806-appb-I000074
Figure PCTKR2013003806-appb-I000074

CORE-1 대신 CORE-3B를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Mat-26 (5.36g, 수율 68%)을 얻었다.Except for using CORE-3B instead of CORE-1 was carried out in the same manner as in Synthesis Example 5 to obtain the target compound Mat-26 (5.36g, yield 68%).

Exact Mass: 657.20g/molExact Mass: 657.20 g / mol

Elemental Analysis: C, 80.34; H, 4.14; N, 10.65; S, 4.87 Elemental Analysis: C, 80.34; H, 4.14; N, 10.65; S, 4.87

[합성예 27] Mat-27의 합성Synthesis Example 27 Synthesis of Mat-27

Figure PCTKR2013003806-appb-I000075
Figure PCTKR2013003806-appb-I000075

CORE-1 대신 CORE-3B를 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 Mat-27 (4.02g, 수율 65%)을 얻었다.Except for using CORE-3B instead of CORE-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound Mat-27 (4.02g, 65% yield).

Exact Mass: 515.15g/molExact Mass: 515.15 g / mol

Elemental Analysis: C, 81.53; H, 4.11; N, 8.15; S, 6.22 Elemental Analysis: C, 81.53; H, 4.11; N, 8. 15; S, 6.22

[합성예 28] Mat-28의 합성Synthesis Example 28 Synthesis of Mat-28

Figure PCTKR2013003806-appb-I000076
Figure PCTKR2013003806-appb-I000076

CORE-1 대신 CORE-3B를 사용하는 것을 제외하고는 합성예 7과 동일한 과정을 수행하여 목적 화합물인 Mat-28 (3.12g, 수율 61%)을 얻었다.Except for using CORE-3B instead of CORE-1 was carried out in the same manner as in Synthesis Example 7 to obtain the target compound Mat-28 (3.12g, 61% yield).

Exact Mass: 427.11g/molExact Mass: 427.11 g / mol

Elemental Analysis: C, 78.66; H, 4.01; N, 9.83; S, 7.50 Elemental Analysis: C, 78.66; H, 4.01; N, 9.83; S, 7.50

[합성예 29] Mat-29의 합성Synthesis Example 29 Synthesis of Mat-29

Figure PCTKR2013003806-appb-I000077
Figure PCTKR2013003806-appb-I000077

CORE-1 대신 CORE-4A를 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 Mat-29 (4.24g, 수율 70%)을 얻었다.Except for using CORE-4A instead of CORE-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound Mat-29 (4.24g, yield 70%).

Exact Mass: 489.16g/molExact Mass: 489.16 g / mol

Elemental Analysis: C, 78.51; H, 3.91; N, 14.31; O, 3.27 Elemental Analysis: C, 78.51; H, 3.91; N, 14.31; O, 3.27

[합성예 30] Mat-30의 합성Synthesis Example 30 Synthesis of Mat-30

Figure PCTKR2013003806-appb-I000078
Figure PCTKR2013003806-appb-I000078

CORE-1 대신 CORE-4A를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Mat-30 (5.00g, 수율 65%)을 얻었다.Except for using CORE-4A instead of CORE-1 was carried out the same procedure as in Synthesis Example 5 to obtain the target compound Mat-30 (5.00g, yield 65%).

Exact Mass: 641.22g/molExact Mass: 641.22 g / mol

Elemental Analysis: C, 82.35; H, 4.24; N, 10.91; O, 2.49 Elemental Analysis: C, 82.35; H, 4. 24; N, 10.91; O, 2.49

[합성예 31] Mat-31의 합성Synthesis Example 31 Synthesis of Mat-31

Figure PCTKR2013003806-appb-I000079
Figure PCTKR2013003806-appb-I000079

CORE-1 대신 CORE-4A를 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 Mat-31 (3.77g, 수율 63%)을 얻었다.Except for using CORE-4A instead of CORE-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound Mat-31 (3.77g, 63% yield).

Exact Mass: 499.17g/molExact Mass: 499.17 g / mol

Elemental Analysis: C, 84.15; H, 4.24; N, 8.41; O, 3.20 Elemental Analysis: C, 84.15; H, 4. 24; N, 8.41; O, 3.20

[합성예 32] Mat-32의 합성Synthesis Example 32 Synthesis of Mat-32

Figure PCTKR2013003806-appb-I000080
Figure PCTKR2013003806-appb-I000080

CORE-1 대신 CORE-4B를 사용하는 것을 제외하고는 합성예 4와 동일한 과정을 수행하여 목적 화합물인 Mat-32 (4.34g, 수율 74%)을 얻었다.Except for using CORE-4B instead of CORE-1 was carried out in the same manner as in Synthesis Example 4 to obtain the target compound Mat-32 (4.34g, 74% yield).

Exact Mass: 489.16g/molExact Mass: 489.16 g / mol

Elemental Analysis: C, 78.51; H, 3.91; N, 14.31; O, 3.27Elemental Analysis: C, 78.51; H, 3.91; N, 14.31; O, 3.27

[합성예 33] Mat-33의 합성Synthesis Example 33 Synthesis of Mat-33

Figure PCTKR2013003806-appb-I000081
Figure PCTKR2013003806-appb-I000081

CORE-1 대신 CORE-4B를 사용하는 것을 제외하고는 합성예 5와 동일한 과정을 수행하여 목적 화합물인 Mat-33 (5.38g, 수율 70%)을 얻었다.Except for using CORE-4B instead of CORE-1 was carried out in the same manner as in Synthesis Example 5 to obtain the target compound Mat-33 (5.38g, yield 70%).

Exact Mass: 641.22g/molExact Mass: 641.22 g / mol

Elemental Analysis: C, 82.35; H, 4.24; N, 10.91; O, 2.49 Elemental Analysis: C, 82.35; H, 4. 24; N, 10.91; O, 2.49

[합성예 34] Mat-34의 합성Synthesis Example 34 Synthesis of Mat-34

Figure PCTKR2013003806-appb-I000082
Figure PCTKR2013003806-appb-I000082

CORE-1 대신 CORE-4B를 사용하는 것을 제외하고는 합성예 6과 동일한 과정을 수행하여 목적 화합물인 Mat-34 (4.07g, 수율 68%)을 얻었다.Except for using CORE-4B instead of CORE-1 was carried out in the same manner as in Synthesis Example 6 to obtain the target compound Mat-34 (4.07g, yield 68%).

Exact Mass: 499.17g/molExact Mass: 499.17 g / mol

Elemental Analysis: C, 84.15; H, 4.24; N, 8.41; O, 3.20Elemental Analysis: C, 84.15; H, 4. 24; N, 8.41; O, 3.20

[실시예 1] 녹색 유기 전계 발광 소자의 제작Example 1 Fabrication of Green Organic Electroluminescent Device

합성예 1에서 합성된 화합물 Mat-1을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후, 하기와 같이 녹색 유기 전계 발광 소자를 제조하였다.The compound Mat-1 synthesized in Synthesis Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic electroluminescent device was manufactured as follows.

ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수로 세척하였다. 증류수 세척이 끝나면, 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음, UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.A glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech), and then wash the substrate using UV for 5 minutes The substrate was transferred to a vacuum evaporator.

상기와 같이 준비된 ITO 투명 기판 위에, 합성예 1의 화합물 Mat-1를 호스트로 이용하여, m-MTDATA(60 nm) / TCTA(80 nm) / 화합물 Mat-1 + 10 % Ir(ppy)3(300nm) / BCP(10 nm) / Alq3(30 nm) / LiF(1 nm) / Al(200 nm) 순으로 적층하여 녹색 유기 전계 발광 소자를 제작하였다.On the prepared ITO transparent substrate, using the compound Mat-1 of Synthesis Example 1 as a host, m-MTDATA (60 nm) / TCTA (80 nm) / compound Mat-1 + 10% Ir (ppy) 3 ( 300 nm) / BCP (10 nm) / Alq 3 (30 nm) / LiF (1 nm) / Al (200 nm) in order to produce a green organic electroluminescent device.

사용된 m-MTDATA, TCTA, Ir(ppy)3 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 and BCP used are as follows.

Figure PCTKR2013003806-appb-I000083
Figure PCTKR2013003806-appb-I000083

Figure PCTKR2013003806-appb-I000084
Figure PCTKR2013003806-appb-I000084

[실시예 2 ~ 34][Examples 2 to 34]

실시예 1에서 발광층 형성시 발광 호스트 물질로서 사용된 화합물 Mat-1 대신 합성예 2 내지 34에서 각각 합성된 화합물 Mat-2 내지 Mat-34를 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 녹색 유기 전계 발광 소자를 제조하였다.The same procedure as in Example 1 was repeated except that the compounds Mat-2 to Mat-34 synthesized in Synthesis Examples 2 to 34 were used instead of the compound Mat-1 to be used as the light emitting host material in Example 1 To produce a green organic electroluminescent device.

[비교예 1]Comparative Example 1

실시예 1에서 발광층 형성시 발광 호스트 물질로서 사용된 화합물 Mat-1 대신 CBP를 사용하는 것을 제외하고는, 실시예 1과 동일하게 수행하여 녹색 유기 전계 발광 소자를 제작하였다. 사용된 CBP의 구조는 하기와 같다.A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound Mat-1 used as the light emitting host material in forming the light emitting layer in Example 1. The structure of CBP used is as follows.

Figure PCTKR2013003806-appb-I000085
Figure PCTKR2013003806-appb-I000085

[실험예]Experimental Example

실시예 1 내지 34 및 비교예 1에서 각각 제조된 녹색 유기 전계 발광 소자에 대하여, 전류밀도 10mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하였고, 그 결과를 하기 표 1에 나타내었다.For green organic electroluminescent devices prepared in Examples 1 to 34 and Comparative Example 1, driving voltage, current efficiency, and emission peak at a current density of 10 mA / cm 2 were measured, and the results are shown in Table 1 below.

표 1 샘플 호스트 구동 전압(V) 발광 피크(nm) 전류효율(cd/A) 실시예 1 Mat-1 6.50 520 41.0 실시예 2 Mat-2 6.61 523 41.2 실시예 3 Mat-3 6.60 523 40.8 실시예 4 Mat-4 6.58 523 41.1 실시예 5 Mat-5 6.70 522 41.8 실시예 6 Mat-6 6.70 520 41.3 실시예 7 Mat-7 6.51 521 41.4 실시예 8 Mat-8 6.66 520 40.9 실시예 9 Mat-9 6.50 520 41.0 실시예 10 Mat-10 6.45 519 41.5 실시예 11 Mat-11 6.60 521 41.3 실시예 12 Mat-12 6.55 518 41.1 실시예 13 Mat-13 6.70 520 41.2 실시예 14 Mat-14 6.50 523 41.3 실시예 15 Mat-15 6.64 520 41.1 실시예 16 Mat-16 6.60 522 41.5 실시예 17 Mat-17 6.62 522 40.9 실시예 18 Mat-18 6.70 520 41.4 실시예 19 Mat-19 6.64 520 41.0 실시예 20 Mat-20 6.50 521 41.6 실시예 21 Mat-21 6.70 520 41.5 실시예 22 Mat-22 6.63 521 41.0 실시예 23 Mat-23 6.70 522 40.9 실시예 24 Mat-24 6.55 520 41.8 실시예 25 Mat-25 6.65 519 40.9 실시예 26 Mat-26 6.60 521 41.1 실시예 27 Mat-27 6.65 520 41.5 실시예 28 Mat-28 6.52 521 41.4 실시예 29 Mat-29 6.79 520 39.8 실시예 30 Mat-30 6.75 519 39.5 실시예 31 Mat-31 6.70 520 39.0 실시예 32 Mat-32 6.81 521 39.2 실시예 33 Mat-33 6.75 521 39.5 실시예 34 Mat-34 6.80 520 39.7 비교예 1 CBP 6.93 516 38.2 Table 1 Sample Host Drive voltage (V) Emission Peak (nm) Current efficiency (cd / A) Example 1 Mat-1 6.50 520 41.0 Example 2 Mat-2 6.61 523 41.2 Example 3 Mat-3 6.60 523 40.8 Example 4 Mat-4 6.58 523 41.1 Example 5 Mat-5 6.70 522 41.8 Example 6 Mat-6 6.70 520 41.3 Example 7 Mat-7 6.51 521 41.4 Example 8 Mat-8 6.66 520 40.9 Example 9 Mat-9 6.50 520 41.0 Example 10 Mat-10 6.45 519 41.5 Example 11 Mat-11 6.60 521 41.3 Example 12 Mat-12 6.55 518 41.1 Example 13 Mat-13 6.70 520 41.2 Example 14 Mat-14 6.50 523 41.3 Example 15 Mat-15 6.64 520 41.1 Example 16 Mat-16 6.60 522 41.5 Example 17 Mat-17 6.62 522 40.9 Example 18 Mat-18 6.70 520 41.4 Example 19 Mat-19 6.64 520 41.0 Example 20 Mat-20 6.50 521 41.6 Example 21 Mat-21 6.70 520 41.5 Example 22 Mat-22 6.63 521 41.0 Example 23 Mat-23 6.70 522 40.9 Example 24 Mat-24 6.55 520 41.8 Example 25 Mat-25 6.65 519 40.9 Example 26 Mat-26 6.60 521 41.1 Example 27 Mat-27 6.65 520 41.5 Example 28 Mat-28 6.52 521 41.4 Example 29 Mat-29 6.79 520 39.8 Example 30 Mat-30 6.75 519 39.5 Example 31 Mat-31 6.70 520 39.0 Example 32 Mat-32 6.81 521 39.2 Example 33 Mat-33 6.75 521 39.5 Example 34 Mat-34 6.80 520 39.7 Comparative Example 1 CBP 6.93 516 38.2

상기 표 1을 살펴보면 본 발명의 화학식 1로 표시되는 화합물(화합물 Mat-1 내지 Mat-34)을 발광층의 호스트 물질로 사용하는 실시예 1 내지 34에서 각각 제조된 녹색 유기 전계 발광 소자는 종래 CBP를 사용하는 비교예 1의 녹색 유기 전계 발광 소자보다 전류효율 및 구동전압 면에서 우수한 성능을 나타내는 것을 확인할 수 있었다.Referring to Table 1, the green organic electroluminescent devices manufactured in Examples 1 to 34, which use the compounds represented by Chemical Formula 1 of the present invention (Compounds Mat-1 to Mat-34) as the host material of the emission layer, respectively, have conventional CBP. It was confirmed that the green organic electroluminescent device of Comparative Example 1 used exhibited superior performance in terms of current efficiency and driving voltage.

본 발명의 화학식 1로 표시되는 화합물을 유기 전계 발광 소자의 유기물층(바람직하게는, 발광층의 발광 물질로)에 사용할 경우, 유기 전계 발광 소자의 효율(발광 효율 및 전령 효율), 수명, 휘도 및 구동전압 등을 향상시킬 수 있다. 따라서, 본 발명은 성능 및 수명이 향상된 풀 칼라 유기 전계 발광 패널을 제공할 수 있다.When the compound represented by Chemical Formula 1 of the present invention is used in an organic material layer (preferably as a light emitting material of the light emitting layer) of the organic electroluminescent device, the efficiency (luminescence efficiency and messenger efficiency), lifetime, brightness and driving of the organic electroluminescent device Voltage and the like can be improved. Accordingly, the present invention can provide a full color organic electroluminescent panel with improved performance and lifespan.

Claims (8)

하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1): [화학식 1][Formula 1]
Figure PCTKR2013003806-appb-I000086
Figure PCTKR2013003806-appb-I000086
 상기 화학식 1에서,In Chemical Formula 1, A는 O 또는 S이고,A is O or S, X1 내지 X4는, 각각 독립적으로, CR1 또는 N이고,X 1 to X 4 are each independently CR 1 or N, Y1과 Y2, Y2와 Y3, Y3와 Y4 중 하나는 하기 화학식 2로 표시되는 화합물과 축합 고리를 형성하고, Y1 내지 Y4 중 축합 고리를 형성하지 않는 것은 CR2 또는 N이고, 이때, N을 반드시 포함하며, One of Y 1 and Y 2 , Y 2 and Y 3 , Y 3 and Y 4 forms a condensed ring with the compound represented by the following formula (2), and those which do not form a condensed ring of Y 1 to Y 4 are CR 2 or N, wherein it must include N, [화학식 2] [Formula 2]
Figure PCTKR2013003806-appb-I000087
Figure PCTKR2013003806-appb-I000087
 상기 화학식 2에서,In Chemical Formula 2, Z1 내지 Z4는, 각각 독립적으로, CR3 또는 N이고,Z 1 to Z 4 are each independently CR 3 or N, 상기 R1 내지 R3는, 각각 독립적으로, 수소, 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, (C6~C40의 아릴)C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고, 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며,R 1 to R 3 are each independently hydrogen, deuterium, halogen, cyano group, C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 2 -C 40 alkynyl group, C 6- C 40 aryl group, nuclear atom 5 to 40 heteroaryl group, C 6 ~ C 40 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 40 arylamine group, (C 6 - of C 40 aryl) C of 1 - C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, and a C 6 ~ C 40 of Selected from the group consisting of arylsilyl groups, may be combined with adjacent groups to form a condensed ring, 상기 Ar1은 수소, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, (C6~C40의 아릴)C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택되고,Ar 1 is hydrogen, C 1 ~ C 40 Alkyl group, C 2 ~ C 40 Alkenyl group, C 2 ~ C 40 Alkynyl group, C 6 ~ C 40 Aryl group, nuclear atoms 5 to 40 heteroaryl C 6 -C 40 aryloxy group, C 1 -C 40 alkyloxy group, C 6 -C 40 arylamine group, (C 6 -C 40 aryl) C 1 -C 40 alkyl group, C of 3 ~ C 40 cycloalkyl group, a 3 to 40 nuclear atoms of a heterocycloalkyl group, an aryl group is selected from the group consisting of silyl C 1 ~ C 40 alkylsilyl group and a C 6 ~ C 40, 상기 R1 내지 R3 및 Ar1의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 아릴아민기, 아릴알킬기, 시클로알킬기, 헤테로시클로알킬기, 알킬실릴기, 및 아릴실릴기는 중수소, 할로겐, 시아노기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C40의 아릴기, 핵원자수 5 내지 40의 헤테로아릴기, C6~C40의 아릴옥시기, C1~C40의 알킬옥시기, C6~C40의 아릴아민기, (C6~C40의 아릴)C1~C40의 알킬기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40의 헤테로시클로알킬기, C1~C40의 알킬실릴기 및 C6~C40의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환될 수 있으며, 치환될 때 각각의 치환기는 동일하거나 상이하다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, arylamine group, arylalkyl group, cycloalkyl group, heterocycloalkyl group, alkylsilyl group of R 1 to R 3 and Ar 1 , And arylsilyl groups are deuterium, halogen, cyano group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 40 aryl group, nuclear atom number 5 to 40 heteroaryl group, C 6 to C 40 aryloxy group, C 1 to C 40 alkyloxy group, C 6 to C 40 arylamine group, (C 6 to C 40 aryl) C 1 ~ one member selected from the group consisting of C 40 alkyl group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkyl silyl group, and a C 6 ~ with an aryl silyl group of C 40 of It may be substituted with more than one substituent, each substituent is the same or different when substituted. 제1항에 있어서,The method of claim 1, 상기 화학식 1로 표시되는 화합물은 하기 화학식 3 내지 8로 표시되는 화합물로 이루어진 군에서 선택된 것이 특징인 화합물: Compound represented by the formula (1) is characterized in that the compound selected from the group consisting of compounds represented by the following formulas 3 to 8: [화학식 3][Formula 3]
Figure PCTKR2013003806-appb-I000088
Figure PCTKR2013003806-appb-I000088
 [화학식 4][Formula 4]
Figure PCTKR2013003806-appb-I000089
Figure PCTKR2013003806-appb-I000089
 [화학식 5][Formula 5]
Figure PCTKR2013003806-appb-I000090
Figure PCTKR2013003806-appb-I000090
 [화학식 6][Formula 6]
Figure PCTKR2013003806-appb-I000091
Figure PCTKR2013003806-appb-I000091
 [화학식 7][Formula 7]
Figure PCTKR2013003806-appb-I000092
Figure PCTKR2013003806-appb-I000092
 [화학식 8][Formula 8]
Figure PCTKR2013003806-appb-I000093
Figure PCTKR2013003806-appb-I000093
 상기 화학식 3 내지 8에서, In Chemical Formulas 3 to 8, A, X1 내지 X4, Y1 내지 Y4, Z1 내지 Z4 및 Ar1은 제1항에서 정의된 바와 동일하다.A, X 1 to X 4 , Y 1 to Y 4, Z 1 to Z 4 and Ar 1 are the same as defined in claim 1 . 제1항에 있어서, The method of claim 1, 상기 화학식 1로 표시되는 화합물은 하기 화학식 C1 내지 C18로 표시되는 화합물로 이루어진 군에서 선택된 것이 특징인 화합물:Compound represented by the formula (1) is characterized in that the compound selected from the group consisting of compounds represented by the formula C1 to C18:
Figure PCTKR2013003806-appb-I000094
Figure PCTKR2013003806-appb-I000094
 상기 화학식 C1 내지 C18에서,In Chemical Formulas C1 to C18, A, X1 내지 X4, Z1 내지 Z4 및 Ar1은 제1항에서 정의된 바와 동일하다.A, X 1 to X 4, Z 1 to Z 4 and Ar 1 are the same as defined in claim 1 . 제3항에 있어서,The method of claim 3, 상기 A는 S인 것이 특징인 화합물.A is a compound characterized in that S. 제1항에 있어서,The method of claim 1, 상기 Ar1은 치환 또는 비치환된 C6~C40의 아릴기, 또는 치환 또는 비치환된 핵원자수 5 내지 40의 헤테로아릴기인 것이 특징인 화합물. Ar 1 is a substituted or unsubstituted C 6 to C 40 aryl group, or a substituted or unsubstituted compound having 5 to 40 heteroaryl atoms. 제1항에 있어서,The method of claim 1, 상기 Ar1은 하기 S-1 내지 S-39로 표시되는 구조로 이루어진 군에서 선택되는 것이 특징인 화합물:Ar 1 is a compound characterized in that it is selected from the group consisting of the structures represented by S-1 to S-39:
Figure PCTKR2013003806-appb-I000095
Figure PCTKR2013003806-appb-I000095
 양극, 음극 및 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자에 있어서,In an organic electroluminescent device comprising an anode, a cathode and at least one organic layer interposed between the anode and the cathode, 상기 1층 이상의 유기물층 중 적어도 하나는 제1항 내지 제6항 중 어느 한 항에 기재된 화합물을 포함하는 것이 특징인 유기 전계 발광 소자.At least one of the one or more organic material layers comprises the compound according to any one of claims 1 to 6. 제7항에 있어서,The method of claim 7, wherein 상기 화합물을 포함하는 유기물층은 발광층인 것이 특징인 유기 전계 발광 소자.The organic material layer containing the compound is an organic electroluminescent device, characterized in that the light emitting layer.
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