WO2018012763A1 - Organic compound and organic electroluminescent device comprising same - Google Patents
Organic compound and organic electroluminescent device comprising same Download PDFInfo
- Publication number
- WO2018012763A1 WO2018012763A1 PCT/KR2017/006856 KR2017006856W WO2018012763A1 WO 2018012763 A1 WO2018012763 A1 WO 2018012763A1 KR 2017006856 W KR2017006856 W KR 2017006856W WO 2018012763 A1 WO2018012763 A1 WO 2018012763A1
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- Prior art keywords
- group
- aryl
- groups
- alkyl
- boron
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- 150000002894 organic compounds Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 256
- 125000003118 aryl group Chemical group 0.000 claims description 127
- 125000000217 alkyl group Chemical group 0.000 claims description 87
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 69
- 125000001072 heteroaryl group Chemical group 0.000 claims description 52
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 51
- 125000004104 aryloxy group Chemical group 0.000 claims description 48
- 125000004429 atom Chemical group 0.000 claims description 48
- 125000003545 alkoxy group Chemical group 0.000 claims description 46
- 125000000304 alkynyl group Chemical group 0.000 claims description 46
- 125000005264 aryl amine group Chemical group 0.000 claims description 44
- 125000005104 aryl silyl group Chemical group 0.000 claims description 44
- 125000001424 substituent group Chemical group 0.000 claims description 44
- 125000000592 heterocycloalkyl group Chemical group 0.000 claims description 43
- 125000005103 alkyl silyl group Chemical group 0.000 claims description 42
- 125000003342 alkenyl group Chemical group 0.000 claims description 40
- 238000000034 method Methods 0.000 claims description 31
- 239000000126 substance Substances 0.000 claims description 30
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 29
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 29
- 229910052736 halogen Inorganic materials 0.000 claims description 29
- 150000002367 halogens Chemical class 0.000 claims description 29
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 29
- 229910052805 deuterium Inorganic materials 0.000 claims description 28
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 claims description 28
- 239000011368 organic material Substances 0.000 claims description 27
- -1 alkyl boron Chemical compound 0.000 claims description 25
- 238000002347 injection Methods 0.000 claims description 23
- 239000007924 injection Substances 0.000 claims description 23
- 125000005328 phosphinyl group Chemical group [PH2](=O)* 0.000 claims description 22
- 229910052757 nitrogen Inorganic materials 0.000 claims description 18
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- 239000001257 hydrogen Substances 0.000 claims description 16
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- 230000005525 hole transport Effects 0.000 claims description 11
- 229910052717 sulfur Inorganic materials 0.000 claims description 11
- 229910052796 boron Inorganic materials 0.000 claims description 10
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 8
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- 230000005281 excited state Effects 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- UIWYJDYFSGRHKR-UHFFFAOYSA-N gadolinium atom Chemical compound [Gd] UIWYJDYFSGRHKR-UHFFFAOYSA-N 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004770 highest occupied molecular orbital Methods 0.000 description 1
- 125000002962 imidazol-1-yl group Chemical group [*]N1C([H])=NC([H])=C1[H] 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910003437 indium oxide Inorganic materials 0.000 description 1
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 1
- 125000001041 indolyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000555 isopropenyl group Chemical group [H]\C([H])=C(\*)C([H])([H])[H] 0.000 description 1
- 239000002346 layers by function Substances 0.000 description 1
- 239000011133 lead Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- PUPKPAZSFZOLOR-UHFFFAOYSA-N n,n-dimethylformamide;toluene Chemical compound CN(C)C=O.CC1=CC=CC=C1 PUPKPAZSFZOLOR-UHFFFAOYSA-N 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 125000002868 norbornyl group Chemical group C12(CCC(CC1)C2)* 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229920006255 plastic film Polymers 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920000128 polypyrrole Polymers 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000001337 psychedelic effect Effects 0.000 description 1
- 125000000561 purinyl group Chemical group N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000002098 pyridazinyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000011135 tin Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
-
- 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
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
- C07D491/056—Ortho-condensed systems with two or more oxygen atoms as ring hetero atoms in the oxygen-containing ring
-
- 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
- C07D495/02—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 two hetero rings
- C07D495/04—Ortho-condensed systems
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- 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]
- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection 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
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
-
- 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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1011—Condensed systems
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- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
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- 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
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1037—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with sulfur
Definitions
- the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
- the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
- the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors.
- a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
- the dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt.
- a metal complex compound containing heavy atoms such as Ir and Pt.
- NPB hole blocking layer
- BCP hole blocking layer
- electron transporting layer material anthracene derivatives have been reported as the light emitting layer material.
- metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which have advantages in terms of efficiency improvement among the light emitting layer materials, are blue, green, and red. (red) is used as the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.
- the conventional organic material has an advantageous aspect in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, development of an organic material layer material excellent in performance is desired.
- 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):
- At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7, and R 7 and R 8 is represented by one of the following Chemical Formulas 2 to 4 Condensed with the ring to form a condensed ring;
- the dotted line is the part where condensation takes place
- X 1 to X 3 are each independently selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), but X 1 to X 3 At least one of is N (Ar 1 );
- Y 1 to Y 6 are each independently N or C (R 9 );
- Ar 1 Ar 5 is each independently C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 3 ⁇ C 40 Cycloalkyl group, 3 to 40 heteroatoms Cycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyl Of silyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 arylphosphanyl group, C 6 ⁇ C 60 selected from mono or diaryl phosphine group P and the group consisting of C 6 ⁇ C 60 aryl amine, or by combining adjacent groups may form a condensed ring;
- R 1 to R 8 and R 9 which do not form a condensed ring with the ring represented by Formula 2 to 4, and R 9 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group of C 1 to C 40 , C of 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 of the alkynyl group, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 To 60 heteroaryl groups, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylpho
- Ar 1 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron of Ar 5 to R 1 to R 9 Group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, an aryloxy group of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ C 60, alkyloxy group of C 1 ⁇ C 40 of the , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40
- 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, at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device comprising a.
- Alkyl in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
- Alkenyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon double bond, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
- Alkynyl in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon triple bond, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.
- Aryl in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined.
- monovalent having two or more rings condensed with each other, containing only carbon as a ring forming atom for example, may have 8 to 60 carbon atoms
- the whole molecule has non-aromacity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.
- Heteroaryl in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, and in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity).
- heteroaryl examples include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
- aryloxy is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms.
- R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
- alkyloxy is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and is linear, branched or cyclic structure.
- alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
- Arylamine in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
- cycloalkyl in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms.
- examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
- Heterocycloalkyl in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se.
- heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
- alkylsilyl means silyl substituted with alkyl having 1 to 40 carbon atoms
- arylsilyl means silyl substituted with aryl having 5 to 60 carbon atoms.
- Condensed ring in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
- the compound represented by Formula 1 of the present invention may be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescence properties.
- an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with improved performance and lifetime can also be manufactured.
- the present invention provides a compound represented by the following formula (1):
- At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7, and R 7 and R 8 is a ring represented by one of the following Chemical Formulas 2 to 4 Condensed with to form a condensed ring;
- the dotted line is the part where condensation takes place
- X 1 to X 3 are each independently selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), but X 1 to X 3 At least one of is N (Ar 1 );
- Y 1 to Y 6 are each independently N or C (R 9 );
- Ar 1 Ar 5 is each independently C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 3 ⁇ C 40 Cycloalkyl group, 3 to 40 heteroatoms Cycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyl Of silyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 arylphosphanyl group, C 6 ⁇ C 60 May be selected from the group consisting of mono or diarylphosphinyl groups and C 6 -C 60 arylamine groups, or can be combined with adjacent groups to form a condensed ring;
- Ar 1 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron of Ar 5 to R 1 to R 9 Group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, an aryloxy group of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ C 60, alkyloxy group of C 1 ⁇ C 40 of the , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40
- novel compounds of the present invention can be represented by the following formula (1):
- the dotted line is the part where condensation takes place
- X 1 to X 3 are each independently selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), but X 1 to X 3 At least one of is N (Ar 1 );
- Y 1 to Y 6 are each independently N or C (R 9 );
- Ar 1 Ar 5 is each independently C 1 ⁇ C 40 Alkyl group, C 2 ⁇ C 40 Alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 3 ⁇ C 40 Cycloalkyl group, 3 to 40 heteroatoms Cycloalkyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 60 aryloxy group, C 1 ⁇ C 40 alkyl Of silyl group, C 6 ⁇ C 60 arylsilyl group, C 1 ⁇ C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 arylphosphanyl group, C 6 ⁇ C 60 May be selected from the group consisting of mono or diarylphosphinyl groups and C 6 -C 60 arylamine groups, or can be combined with adjacent groups to form a condensed ring;
- R 1 to R 8 and R 9 which do not form a condensed ring with the ring represented by Formula 2 to 4, and R 9 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group of C 1 to C 40 , C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 To 60 heteroaryl groups, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 ⁇ C 60 aryl boron group, C 6 ⁇ C 60 aryl phosphazene group, C 6 ⁇ C 60 mono or diaryl Phosphinicosuccinic aryl group and a
- Ar 1 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron of Ar 5 to R 1 to R 9 Group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenes group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, an aryloxy group of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ C 60, alkyloxy group of C 1 ⁇ C 40 of the , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40
- the compound represented by Chemical Formula 1 of the present invention has a higher molecular weight than the conventional organic electroluminescent device material (for example, 4,4-dicarbazolyl biphenyl (hereinafter referred to as 'CBP')), the glass transition temperature It is high in not only excellent thermal stability but also excellent carrier transport ability, luminous ability, etc. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage, efficiency, lifespan, etc. of the device may be improved.
- the conventional organic electroluminescent device material for example, 4,4-dicarbazolyl biphenyl (hereinafter referred to as 'CBP')
- the glass transition temperature It is high in not only excellent thermal stability but also excellent carrier transport ability, luminous ability, etc. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage, efficiency, lifespan, etc. of the device may be improved.
- the host material should have a triplet energy gap of which is higher than the triplet energy gap of the dopant. That is, when the lowest excited state of the host is higher in energy than the lowest emitted state of the dopant, phosphorescence efficiency may be improved.
- the compound of Formula 1 may be used as a phosphorescent host material by introducing a specific substituent into the basic skeleton having a triplet energy, the energy level can be adjusted higher than the dopant.
- the compound of Formula 1 may adjust HOMO and LUMO energy levels according to the type of substituents introduced into the basic skeleton, may have a wide bandgap, it may have a high carrier transport.
- EWG electron-withdrawing electron
- the compound is bonded to an electron-withdrawing electron (EWG) having a high electron absorption such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.) to the basic skeleton, Since it has a bipolar characteristic, it is possible to increase the bonding force between the hole and the electron.
- EWG electron-withdrawing electron
- the compound of Formula 1 having EWG introduced into the basic skeleton has excellent carrier transport properties and luminescent properties, and thus, as an electron injection / transport layer material or a life improvement layer material, in addition to the light emitting layer material of the organic EL device. Can be used.
- an electron donor group EWG
- the hole injection and transport is smooth.
- it can be usefully used as a hole injection / transport layer or a light emitting auxiliary layer material.
- the compound represented by Chemical Formula 1 may improve the light emission characteristics of the organic EL device, and may also improve the hole injection / transport ability, the electron injection / transport capability, the luminous efficiency, the driving voltage, and the lifespan characteristics.
- the compound of formula 1 according to the present invention is an organic material layer material of the organic electroluminescent device, preferably a light emitting layer material (green and / or red phosphorescent host material), electron transport / injection layer material and hole transport / injection layer material, It can be used as the light emitting auxiliary layer material, life improvement layer material, more preferably light emitting layer material, electron injection layer material, light emitting auxiliary layer material, life improving layer material.
- the compound of Formula 1 has a variety of substituents, especially aryl groups and / or heteroaryl groups introduced into the basic skeleton significantly increases the molecular weight of the compound, thereby improving the glass transition temperature, thereby conventional light emission It may have a higher thermal stability than the material (eg CBP).
- the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer. Therefore, the organic electroluminescent device including the compound of Formula 1 according to the present invention can greatly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied can also maximize its performance.
- the compound may be a compound represented by any one of the following Formulas A-1 to A-9:
- X 1 to X 3 , R 1 to R 6 , R 8 and Y 1 to Y 6 are each as defined in Chemical Formulas 1 to 4 above.
- R 1 to R 9 and Ar 1 To at least one of Ar 5 is a substituent represented by the following formula (5), wherein R 1 to R 9 and Ar 1 And Ar 5 may be the same or different from each other:
- L 1 and L 2 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
- R 10 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ⁇ C 40 Alkylsilyl group, C 6 ⁇ C 60 Arylsilyl group, C 1 ⁇ C 40 Alkyl boron group, C 6 ⁇ C 60 Aryl boron group, C 6 ⁇ C 60 Aryl phospha A aryl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;
- the amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40
- Ar 1 And at least one of R 9 may be a substituent represented by Formula 5, in which case Ar 1 And R 9 may be the same or different from one another. More preferably, Ar 1 may be a substituent represented by Formula 5.
- L 1 and L 2 are each independently a single bond or a linker represented by any one of the following formulas B-1 to B-6 is preferable in the luminous efficiency and driving voltage characteristics:
- X 4 and X 5 are each independently O, S, N (Ar 6 ) or C (Ar 7 ) (Ar 8 );
- X 6 is N or C (Ar 9 );
- p is an integer from 0 to 4.
- R 11 is heavy hydrogen, a halogen, a cyano group, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, a cycloalkyl group of C 2 ⁇ C 40 alkynyl group, C 3 ⁇ C 40 of nuclear atoms 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C An alkylsilyl group of 3 to C 40 , an arylsilyl group of C 6 to C 60 , an alkyl boron group of C 1 to C 40, an aryl boron group of C 6 to C 60 , an arylphosphanyl group of C 6 to C 60 , A C 6 ⁇ C 60 mono or diaryl phosphinyl group and C 6 ⁇ C 60 arylamine group may be selected from the group consisting of or
- Ar 6 to Ar 9 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, selected from the group consisting arylsilyl a C 6 ⁇ C 60 mono or diaryl phosphine blood group and a C 6 ⁇ C 60 of, or by combining tile adjacent to which they are attached may form a con
- R 10 is hydrogen, an alkyl group of C 1 ⁇ C 40 , an aryl group of C 6 ⁇ C 60 , a heteroaryl group of 5 to 60 nuclear atoms and C 6 ⁇ C 60 It may be selected from the group consisting of arylamine groups.
- the R 10 is hydrogen or a substituent represented by any one of the following formulas C-1 to C-7 is preferable in the luminous efficiency and driving voltage characteristics:
- Z 1 to Z 5 are each independently N or C (R 16);
- T 1 and T 2 are each independently selected from the group consisting of a single bond, C (R 17 ) (R 18 ), N (R 19 ), O and S, but not both T 1 and T 2 are single bonds;
- q and r are each independently integers of 0 to 4.
- R 12 and R 13 are each independently deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of C 6 ⁇ C 60, C 1 ⁇ C 40 alkyloxy group of, C 3 ⁇ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 An arylphosphanyl group, a C 6 ⁇ C 60 mono or diaryl phosphinyl group and a C 6 ⁇ C 60 arylsilyl group, or
- R 14 to R 19 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ⁇ aryloxy C 60, C 1 ⁇ C 40 alkyloxy group of, C 3 ⁇ C 40 cycloalkyl group, a nuclear atoms 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, selected from the group consisting of C 6 ⁇ C 60 mono or diaryl the Phosphinicosuccinic group and a C 6 ⁇ with an aryl silyl group of
- Alkyl group of said R 12 to R 19, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ⁇ C 60 arylamine group, C 3 ⁇ C 40
- R 10 may be a substituent represented by any one of Formulas C-1 to C-5.
- R 14 and R 15 are each independently hydrogen, an alkyl group of C 1 ⁇ C 40 , an aryl group of C 6 ⁇ C 60 , a heteroaryl group of 5 to 60 nuclear atoms and It may be selected from the group consisting of C 6 ⁇ C 60 arylamine group.
- R 14 and R 15 may be each independently selected from the group consisting of a phenyl group, a biphenyl group and a naphthalenyl group.
- R 10 may be a substituent represented by any one of the following Formulas D-1 to D-24:
- t is an integer from 0 to 5
- u is an integer from 0 to 4.
- v is an integer from 0 to 3;
- w is an integer from 0 to 2;
- R 20 is deuterium, halogen, cyano group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 60 aryl group, nuclear atom C 5 to C 60 aryloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 ⁇ mono or diaryl phosphine of C 60 blood group and a C 6 ⁇ C 60 selected from an aryl silyl group the group consisting of or of, by combining groups of adjacent, may form a fused
- R 12 , R 13 , R 16 to R 19 , q and r are each as defined in Chemical Formulas C-1 to C-7.
- the R 12, R 13 and R 20 are each independently a C 1 ⁇ C 40 alkyl group, C 6 ⁇ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group And it may be selected from the group consisting of C 6 ⁇ C 60 arylamine group.
- R 12 , R 13 and R 20 may be each independently selected from the group consisting of a phenyl group, a biphenyl group and a naphthalenyl group.
- Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
- an organic electroluminescent device comprising a compound represented by the formula (1).
- the present invention includes (i) an anode, (ii) a cathode and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers is It includes a compound represented by the formula (1).
- the compound represented by Formula 1 may be used alone or two or more kinds are mixed.
- the one or more organic material layers may include 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, wherein at least one organic material layer is represented by the formula (1) It may include a compound.
- the organic material layer including the compound represented by Formula 1 may be a light emitting layer or a hole transport layer, and more preferably, when the compound represented by Formula 1 is included in the light emitting layer, the luminous efficiency and luminance of the organic EL device It can greatly improve power efficiency, thermal stability and device life.
- the compound represented by Chemical Formula 1 may be a phosphorescent host, a fluorescent host, or a dopant material of the light emitting layer, and preferably, a phosphorescent host of the light emitting layer.
- the one or more organic material layers may include any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by the formula (1).
- the organic material layer including the compound represented by Chemical Formula 1 may be a light emission auxiliary layer.
- the efficiency (light emitting efficiency and power efficiency), lifetime, and luminance of the organic light emitting diode are further improved, and the driving voltage is further improved. Can be lowered.
- the one or more organic material layers may include any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer May include a compound represented by Chemical Formula 1.
- the organic material layer including the compound represented by Formula 1 may be an electron transport auxiliary layer.
- the efficiency (light emitting efficiency and power efficiency), lifespan and luminance of the organic electroluminescent device are further improved, and the driving voltage is more fragile. Can be.
- the structure of the organic EL device of the present invention is not particularly limited, and for example, the anode, one or more organic material layers and the cathode are sequentially stacked on the substrate, and an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer. Can be.
- the organic EL device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked on a substrate, and, if necessary, between the hole transport layer and the light emitting layer.
- An emission auxiliary layer may be inserted, and an electron injection layer may be positioned on the electron transport layer.
- the organic electroluminescent device of the present invention is at least one of the one or more organic material layers, for example, a light emitting layer or a light emitting auxiliary layer is formed so as to include a compound represented by the formula (1), and materials known in the art It can be prepared by forming an organic material layer and an electrode using a method.
- the organic material layer may be formed by a vacuum deposition method or a solution coating method.
- the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
- Examples of the substrate that can be used in the manufacture of the organic EL device in the present invention include a silicon wafer, quartz or glass plate, a metal plate, a plastic film or sheet, but is not limited thereto.
- examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.
- metals such as vanadium, chromium, copper, zinc and gold or alloys thereof.
- Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
- Conductive polymers such as polythiophene, poly (3-methylthiophene
- examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
- the material used as the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and any material known in the art may be used without limitation.
- a compound Cpd 211 (12.0 g, yield 74%) was obtained by performing the same process as in Example 2, but using compound Inv 3 instead of compound Inv 2.
- a glass substrate coated with ITO Indium tin oxide having a thickness of 1500 ⁇ was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
- ITO Indium tin oxide
- UV OZONE cleaner Power sonic 405, Hwasin Tech
- a green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound Cpd 4 synthesized in Reaction Example 1 as a light emitting host material.
- Example 1 Cpd 4 6.82 518 39.9
- Example 2 Cpd 10 6.98 517 40.2
- Example 3 Cpd 11 6.89 515 38.4
- Example 4 Cpd 28 6.78 518 42.4
- Example 5 Cpd 34 6.69 518 42.8
- Example 6 Cpd 35 6.72 517 41.7
- Example 7 Cpd 52 6.70 515 42.0
- Example 8 Cpd 58 6.82 518 40.3
- Example 9 Cpd 59 6.84 518 41.2
- Example 10 Cpd 76 7.20 525 36.4
- Example 11 Cpd 82 6.82 518 39.9
- Example 12 Cpd 83 6.98 517 40.2
- Example 13 Cpd 100 6.89 515 38.4
- Example 14 Cpd 106 6.78 518 41.4
- Example 15 Cpd 107 6.69 518 42.3
- Example 16 Cpd 124 6.72 517 41.7
- Example 17 Cpd 130 6.70 515 41.3
- Example 18 Cp
- the green organic electroluminescent devices of Examples 1 to 36 each using the compound according to the present invention as a light emitting layer material compared to the green organic electroluminescent device of Comparative Example 1 using the conventional CBP And better performance in terms of driving voltage.
- a glass substrate coated with ITO Indium tin oxide having a thickness of 1500 ⁇ was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
- ITO Indium tin oxide
- UV OZONE cleaner Power sonic 405, Hwasin Tech
- a red organic electroluminescent device was manufactured in the same manner as in Example 37, except for using CBP instead of the compound Cpd 19 synthesized in Reaction Example 2 as a light emitting host material.
- Example 37 Cpd 19 4.59 12.8
- Example 38 Cpd 24 4.65 12.0
- Example 39 Cpd 43 4.92 10.4
- Example 40 Cpd 48 4.87 9.4
- Example 41 Cpd 67 4.90 9.8
- Example 42 Cpd 72 4.77 11.5
- Example 43 Cpd 91 4.72 10.2
- Example 44 Cpd 96 4.80 11.0
- Example 45 Cpd 115 4.59 12.8
- Example 46 Cpd 120 4.65 12.0
- Example 47 Cpd 139 4.92 10.4
- Example 48 Cpd 144 4.87 9.4
- Example 49 Cpd 163 4.90 9.8
- Example 50 Cpd 168 4.82 11.5
- Example 51 Cpd 187 4.72 10.2
- Example 52 Cpd 192 4.77 10.8
- Example 53 Cpd 211 4.80 10.4
- Example 45 Cpd 235 4.65 12.0
- Example 46 Cpd 240 4.92 10.4
- Example 47 Cpd 259 4.87 9.4
- the present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
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Abstract
The present invention relates to a novel compound and an organic electroluminescent device comprising same. The compound, according to the present invention, can be used in an organic layer, preferably a light-emitting layer, of an organic electroluminescent device and can enhance the light-emitting efficiency, driving voltage, life and the like of the organic electroluminescent device.
Description
본 발명은 유기 전계 발광 소자용 재료로서 사용될 수 있는 신규 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
1950년대 베르나소스(Bernanose)의 유기 박막 발광 관측을 시점으로 하여, 1965년 안트라센 단결정을 이용한 청색 전기발광으로 이어진 유기 전계 발광(electroluminescent, EL) 소자에 대한 연구가 이어져 오다가, 1987년 탕(Tang)에 의하여 정공층과 발광층의 기능층으로 나눈 적층구조의 유기 전계 발광 소자가 제시되었다. 이후, 고효율, 고수명의 유기 전계 발광 소자를 만들기 위하여, 소자 내 각각의 특징적인 유기물층을 도입하는 형태로 발전하여 왔으며, 이에 사용되는 특화된 물질의 개발로 이어졌다.Investigating organic electroluminescent (EL) devices that led to blue electroluminescence using anthracene single crystals in 1965, based on observation of Bernanose's organic thin-film emission, followed by Tang in 1987. ), An organic EL device having a laminated structure divided into a functional layer of a hole layer and a light emitting layer is proposed. Since then, in order to make a high efficiency, high-life organic electroluminescent device, it has been developed in the form of introducing each characteristic organic material layer in the device, leading to the development of specialized materials used therein.
유기 전계 발광 소자는 두 전극 사이에 전압을 걸어주면 양극에서는 정공이 유기물층으로 주입되고, 음극에서는 전자가 유기물층으로 주입된다. 주입된 정공과 전자가 만났을 때 엑시톤(exciton)이 형성되며, 이 엑시톤이 바닥상태로 떨어질 때 빛이 나게 된다. 이때, 유기물층으로 사용되는 물질은 그 기능에 따라, 발광물질, 정공주입 물질, 정공수송 물질, 전자수송 물질, 전자주입 물질 등으로 분류될 수 있다.In the organic electroluminescent device, when a voltage is applied between two electrodes, holes are injected into the organic material layer at the anode, and electrons are injected into the organic material layer at the cathode. When the injected holes and electrons meet, excitons are formed, and when the excitons fall to the ground, they shine. In this case, the material used as the organic material layer may be classified into a light emitting material, a hole injection material, a hole transport material, an electron transport material, an electron injection material and the like according to its function.
발광 물질은 발광색에 따라 청색, 녹색, 적색 발광 물질과, 보다 나은 천연색을 구현하기 위한 노란색 및 주황색 발광 물질로 구분될 수 있다. 또한, 색순도의 증가와 에너지 전이를 통한 발광 효율을 증가시키기 위하여, 발광 물질로서 호스트/도펀트 계를 사용할 수 있다.The light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials for better natural colors according to light emission colors. In addition, a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
도펀트 물질은 유기 물질을 사용하는 형광 도펀트와 Ir, Pt 등의 중원자(heavy atoms)가 포함된 금속 착체 화합물을 사용하는 인광 도펀트로 나눌 수 있다. 이때, 인광 재료의 개발은 이론적으로 형광에 비해 4배까지 발광 효율을 향상시킬 수 있기 때문에, 인광 도펀트 뿐만 아니라 인광 호스트 재료들에 대한 연구도 많이 진행되고 있다.The dopant material may be divided into a fluorescent dopant using an organic material and a phosphorescent dopant using a metal complex compound containing heavy atoms such as Ir and Pt. At this time, since the development of the phosphorescent material can theoretically improve the luminous efficiency up to 4 times compared to the fluorescence, studies on phosphorescent host materials as well as phosphorescent dopants have been conducted.
현재까지 정공 주입층, 정공 수송층. 정공 차단층, 전자 수송층 재료로는 NPB, BCP, Alq3 등이 널리 알려져 있으며, 발광층 재료로는 안트라센 유도체들이 보고되고 있다. 특히, 발광층 재료 중 효율 향상 측면에서 장점을 가지고 있는 Firpic, Ir(ppy)3, (acac)Ir(btp)2 등과 같은 Ir을 포함하는 금속 착체 화합물이 청색(blue), 녹색(green), 적색(red)의 인광 도판트 재료로 사용되고 있으며, 4,4-디카바졸리비페닐(4,4-dicarbazolybiphenyl, CBP)은 인광 호스트 재료로 사용되고 있다.Hole injection layer, hole transport layer to date. NPB, BCP, Alq 3 and the like are widely known as the hole blocking layer and the electron transporting layer material, and anthracene derivatives have been reported as the light emitting layer material. Particularly, metal complex compounds containing Ir such as Firpic, Ir (ppy) 3 , and (acac) Ir (btp) 2 , which have advantages in terms of efficiency improvement among the light emitting layer materials, are blue, green, and red. (red) is used as the phosphorescent dopant material, 4,4-dicarbazolybiphenyl (CBP) is used as the phosphorescent host material.
그러나 종래의 유기물층 재료들은 발광 특성 측면에서는 유리한 면이 있으나, 유리전이온도가 낮아 열적 안정성이 매우 좋지 않기 때문에, 유기 전계 발광 소자의 수명 측면에서 만족할 만한 수준이 되지 못하고 있다. 따라서, 성능이 뛰어난 유기물층 재료의 개발이 요구되고 있다.However, the conventional organic material has an advantageous aspect in terms of light emission characteristics, but the thermal stability is not very good due to the low glass transition temperature, it is not a satisfactory level in terms of the life of the organic EL device. Therefore, development of an organic material layer material excellent in performance is desired.
본 발명은 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]
상기 화학식 1에서,In Chemical Formula 1,
*R1과 R2, R2와 R3, R3와 R4, R5와 R6, R6과 R7 및 R7과 R8 중 적어도 하나는 하기 화학식 2 내지 4 중 어느 하나로 표시되는 고리와 축합되어 축합 고리를 형성하며;At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7, and R 7 and R 8 is represented by one of the following Chemical Formulas 2 to 4 Condensed with the ring to form a condensed ring;
[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
상기 화학식 1 내지 4에서, In Chemical Formulas 1 to 4,
점선은 축합이 이루어지는 부분이며;The dotted line is the part where condensation takes place;
X1 내지 X3는 각각 독립적으로 O, S, N(Ar1), C(Ar2)(Ar3) 및 Si(Ar4)(Ar5)로 구성된 군으로부터 선택되나, X1 내지 X3 중 적어도 하나는 N(Ar1)이고;X 1 to X 3 are each independently selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), but X 1 to X 3 At least one of is N (Ar 1 );
Y1 내지 Y6은 각각 독립적으로 N 또는 C(R9)이며;Y 1 to Y 6 are each independently N or C (R 9 );
Ar1
내지 Ar5는 각각 독립적으로 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접한 기와 결합하여 축합 고리를 형성할 수 있고;Ar 1 Ar 5 is each independently C 1 ~ C 40 Alkyl group, C 2 ~ C 40 Alkenyl group, C 2 ~ C 40 Alkynyl group, C 3 ~ C 40 Cycloalkyl group, 3 to 40 heteroatoms Cycloalkyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyl Of silyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 selected from mono or diaryl phosphine group P and the group consisting of C 6 ~ C 60 aryl amine, or by combining adjacent groups may form a condensed ring;
상기 화학식 2 내지 4로 표시되는 고리와 축합 고리를 형성하지 않는 R1 내지 R8와, R9는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R9가 복수 개인 경우 복수 개의 R9는 서로 동일하거나 상이하며; R 1 to R 8 and R 9 which do not form a condensed ring with the ring represented by Formula 2 to 4, and R 9 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group of C 1 to C 40 , C of 2 ~ C 40 alkenyl group, C 2 ~ C 40 of the alkynyl group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 To 60 heteroaryl groups, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group and C 6 to C 60 arylamine group is selected from the group consisting of, wherein R 9, when a plurality of individual plurality of R 9 is the same as or different from each other;
상기 Ar1
내지 Ar5 및 R1 내지 R9의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴아민기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.Ar 1 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron of Ar 5 to R 1 to R 9 Group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenes group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, an aryloxy group of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60, alkyloxy group of C 1 ~ C 40 of the , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group , C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group When substituted or unsubstituted with one or more selected substituents and substituted with a plurality of substituents, they are the same or different from each other.
또, 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 중에서 적어도 하나는 전술한 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.In addition, 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, at least one of the at least one organic layer is a compound represented by the formula (1) It provides an organic electroluminescent device comprising a.
본 발명에서의 "알킬"은 탄소수 1 내지 40개의 직쇄 또는 측쇄의 포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 메틸, 에틸, 프로필, 이소부틸, sec-부틸, 펜틸, iso-아밀, 헥실 등이 있는데, 이에 한정되지 않는다."Alkyl" in the present invention is a monovalent substituent derived from a straight or branched chain saturated hydrocarbon having 1 to 40 carbon atoms, examples of which are methyl, ethyl, propyl, isobutyl, sec-butyl, pentyl, iso-amyl and hexyl And the like, but are not limited thereto.
본 발명에서의 "알케닐(alkenyl)"은 탄소-탄소 이중 결합을 1개 이상 가진, 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 비닐(vinyl), 알릴(allyl), 이소프로펜일(isopropenyl), 2-부텐일(2-butenyl) 등이 있는데, 이에 한정되지 않는다."Alkenyl" in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon double bond, and examples thereof include vinyl, Allyl, isopropenyl, 2-butenyl, and the like, but is not limited thereto.
본 발명에서의 "알키닐(alkynyl)"은 탄소-탄소 삼중 결합을 1개 이상 가진, 탄소수 2 내지 40개의 직쇄 또는 측쇄의 불포화 탄화수소에서 유래되는 1가의 치환기이며, 이의 예로는 에티닐(ethynyl), 2-프로파닐(2-propynyl) 등이 있는데, 이에 한정되지 않는다."Alkynyl" in the present invention is a monovalent substituent derived from a C2-C40 straight or branched chain unsaturated hydrocarbon having at least one carbon-carbon triple bond, examples of which are ethynyl. , 2-propynyl, and the like, but is not limited thereto.
본 발명에서의 "아릴"은 단독 고리 또는 2 이상의 고리가 조합된, 탄소수 6 내지 60개의 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 또한, 2 이상의 고리가 서로 축합되어 있고, 고리 형성 원자로서 탄소만을 포함(예를 들어, 탄소수는 8 내지 60개일 수 있음)하고, 분자 전체가 비-방향족성(non-aromacity)를 갖는 1가 치환기도 포함될 수 있다. 이러한 아릴의 예로는 페닐, 나프틸, 페난트릴, 안트릴, 플루오레닐 등이 있는데, 이에 한정되지 않는다."Aryl" in the present invention means a monovalent substituent derived from an aromatic hydrocarbon having 6 to 60 carbon atoms in which a single ring or two or more rings are combined. In addition, monovalent having two or more rings condensed with each other, containing only carbon as a ring forming atom (for example, may have 8 to 60 carbon atoms), and the whole molecule has non-aromacity Substituents may also be included. Examples of such aryl include, but are not limited to, phenyl, naphthyl, phenanthryl, anthryl, fluorenyl, and the like.
본 발명에서의 "헤테로아릴"은 핵원자수 5 내지 60개의 모노헤테로사이클릭 또는 폴리헤테로사이클릭 방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이때, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, P, S 및 Se 중에서 선택된 헤테로원자로 치환된다. 또한, 2 이상의 고리가 서로 단순 부착(pendant)되거나 축합되어 있고, 고리 형성 원자로서 탄소 외에 N, O, P, S 및 Se 중에서 선택된 헤테로 원자를 포함하고, 분자 전체가 비-방향족성(non-aromacity)를 갖는 1가 그룹도 포함하는 것으로 해석된다. 이러한 헤테로아릴의 예로는 피리딜, 피라지닐, 피리미디닐, 피리다지닐, 트리아지닐과 같은 6-원 모노사이클릭 고리; 페녹사티에닐(phenoxathienyl), 인돌리지닐(indolizinyl), 인돌릴(indolyl), 퓨리닐(purinyl), 퀴놀릴(quinolyl), 벤조티아졸(benzothiazole), 카바졸릴(carbazolyl)과 같은 폴리사이클릭 고리; 2-퓨라닐, N-이미다졸릴, 2-이속사졸릴, 2-피리디닐, 2-피리미디닐 등이 있는데, 이에 한정되지 않는다."Heteroaryl" in the present invention means a monovalent substituent derived from a monoheterocyclic or polyheterocyclic aromatic hydrocarbon having 5 to 60 nuclear atoms. At least one carbon in the ring, preferably 1 to 3 carbons, is substituted with a heteroatom selected from N, O, P, S and Se. In addition, two or more rings are simply pendant or condensed with each other, and in addition to carbon as a ring forming atom, a hetero atom selected from N, O, P, S and Se, the entire molecule is non-aromatic (non- It is also interpreted to include monovalent groups having aromacity). Examples of such heteroaryl include 6-membered monocyclic rings such as pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, triazinyl; Polycyclics such as phenoxathienyl, indolinzinyl, indolyl, purinyl, quinolyl, benzothiazole, carbazolyl ring; 2-furanyl, N-imidazolyl, 2-isoxazolyl, 2-pyridinyl, 2-pyrimidinyl, and the like, but are not limited thereto.
본 발명에서의 "아릴옥시"는 RO-로 표시되는 1가의 치환기로, 상기 R은 탄소수 5 내지 60개의 아릴을 의미한다. 이러한 아릴옥시의 예로는 페닐옥시, 나프틸옥시, 디페닐옥시 등이 있는데, 이에 한정되지 않는다.In the present invention, "aryloxy" is a monovalent substituent represented by RO-, wherein R means aryl having 5 to 60 carbon atoms. Examples of such aryloxy include, but are not limited to, phenyloxy, naphthyloxy, diphenyloxy, and the like.
본 발명에서의 "알킬옥시"는 R'O-로 표시되는 1가의 치환기로, 상기 R'는 1 내지 40개의 알킬을 의미하며, 직쇄(linear), 측쇄(branched) 또는 사이클릭(cyclic) 구조를 포함하는 것으로 해석한다. 이러한 알킬옥시의 예로는 메톡시, 에톡시, n-프로폭시, 1-프로폭시, t-부톡시, n-부톡시, 펜톡시 등이 있는데, 이에 한정되지 않는다.In the present invention, "alkyloxy" is a monovalent substituent represented by R'O-, wherein R 'means 1 to 40 alkyl, and is linear, branched or cyclic structure. Interpret as including. Examples of such alkyloxy include, but are not limited to, methoxy, ethoxy, n-propoxy, 1-propoxy, t-butoxy, n-butoxy, pentoxy and the like.
본 발명에서의 "아릴아민"은 탄소수 6 내지 60개의 아릴로 치환된 아민을 의미한다."Arylamine" in the present invention means an amine substituted with aryl having 6 to 60 carbon atoms.
본 발명에서의 "시클로알킬"은 탄소수 3 내지 40개의 모노사이클릭 또는 폴리사이클릭 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미한다. 이러한 사이클로알킬의 예로는 사이클로프로필, 사이클로펜틸, 사이클로헥실, 놀보닐(norbornyl), 아다만틴(adamantine) 등이 있는데, 이에 한정되지 않는다.By "cycloalkyl" in the present invention is meant monovalent substituents derived from monocyclic or polycyclic non-aromatic hydrocarbons having 3 to 40 carbon atoms. Examples of such cycloalkyl include, but are not limited to, cyclopropyl, cyclopentyl, cyclohexyl, norbornyl, adamantine, and the like.
본 발명에서의 "헤테로시클로알킬"은 핵원자수 3 내지 40개의 비-방향족 탄화수소로부터 유래된 1가의 치환기를 의미하며, 고리 중 하나 이상의 탄소, 바람직하게는 1 내지 3개의 탄소가 N, O, S 또는 Se와 같은 헤테로 원자로 치환된다. 이러한 헤테로시클로알킬의 예로는 모르폴린, 피페라진 등이 있는데, 이에 한정되지 않는다."Heterocycloalkyl" in the present invention means a monovalent substituent derived from 3 to 40 non-aromatic hydrocarbons of nuclear atoms, and at least one carbon in the ring, preferably 1 to 3 carbons is N, O, Substituted with a hetero atom such as S or Se. Examples of such heterocycloalkyl include, but are not limited to, morpholine, piperazine, and the like.
본 발명에서의 "알킬실릴"은 탄소수 1 내지 40개의 알킬로 치환된 실릴이고, "아릴실릴"은 탄소수 5 내지 60개의 아릴로 치환된 실릴을 의미한다.In the present invention, "alkylsilyl" means silyl substituted with alkyl having 1 to 40 carbon atoms, and "arylsilyl" means silyl substituted with aryl having 5 to 60 carbon atoms.
본 발명에서의 "축합 고리"는 축합 지방족 고리, 축합 방향족 고리, 축합 헤테로지방족 고리, 축합 헤테로방향족 고리 또는 이들의 조합된 형태를 의미한다."Condensed ring" in the present invention means a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring, a condensed heteroaromatic ring or a combination thereof.
본 발명의 화학식 1로 표시되는 화합물은 열적 안정성 및 발광 특성이 우수하기 때문에 유기 전계 발광 소자의 유기물층의 재료로 사용될 수 있다. 특히, 본 발명의 화학식 1로 표시되는 화합물을 인광 호스트 재료로 사용할 경우, 종래의 호스트 재료에 비해 우수한 발광 성능, 낮은 구동전압, 높은 효율 및 장수명을 갖는 유기 전계 발광 소자를 제조할 수 있고, 나아가 성능 및 수명이 향상된 풀 칼라 디스플레이 패널도 제조할 수 있다.The compound represented by Formula 1 of the present invention may be used as a material of the organic material layer of the organic electroluminescent device because of its excellent thermal stability and luminescence properties. In particular, when the compound represented by Formula 1 of the present invention is used as a phosphorescent host material, an organic electroluminescent device having excellent light emission performance, low driving voltage, high efficiency, and long life compared to a conventional host material can be manufactured. Full color display panels with improved performance and lifetime can also be manufactured.
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]
상기 화학식 1에서,In Chemical Formula 1,
R1과 R2, R2와 R3, R3와 R4, R5와 R6, R6과 R7 및 R7과 R8 중 적어도 하나는 하기 화학식 2 내지 4 중 어느 하나로 표시되는 고리와 축합되어 축합 고리를 형성하며;At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7, and R 7 and R 8 is a ring represented by one of the following Chemical Formulas 2 to 4 Condensed with to form a condensed ring;
[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
상기 화학식 1 내지 4에서, In Chemical Formulas 1 to 4,
점선은 축합이 이루어지는 부분이며;The dotted line is the part where condensation takes place;
X1 내지 X3는 각각 독립적으로 O, S, N(Ar1), C(Ar2)(Ar3) 및 Si(Ar4)(Ar5)로 구성된 군으로부터 선택되나, X1 내지 X3 중 적어도 하나는 N(Ar1)이고;X 1 to X 3 are each independently selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), but X 1 to X 3 At least one of is N (Ar 1 );
Y1 내지 Y6은 각각 독립적으로 N 또는 C(R9)이며;Y 1 to Y 6 are each independently N or C (R 9 );
Ar1
내지 Ar5는 각각 독립적으로 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접한 기와 결합하여 축합 고리를 형성할 수 있고;Ar 1 Ar 5 is each independently C 1 ~ C 40 Alkyl group, C 2 ~ C 40 Alkenyl group, C 2 ~ C 40 Alkynyl group, C 3 ~ C 40 Cycloalkyl group, 3 to 40 heteroatoms Cycloalkyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyl Of silyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 May be selected from the group consisting of mono or diarylphosphinyl groups and C 6 -C 60 arylamine groups, or can be combined with adjacent groups to form a condensed ring;
상기 화학식 2 내지 4로 표시되는 고리와 축합 고리를 형성하지 않는 R1 내지 R8와, R9는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R9가 복수 개인 경우 복수 개의 R9는 서로 동일하거나 상이하며; R 1 to R 8 and R 9 which do not form a condensed ring with the ring represented by Formula 2 to 4, and R 9 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group of C 1 to C 40 , C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 To 60 heteroaryl groups, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 to C 60 mono or diarylphosphinyl group and C 6 to C 60 arylamine group is selected from the group consisting of, wherein R 9, when a plurality of individual plurality of R 9 is the same as or different from each other;
상기 Ar1
내지 Ar5 및 R1 내지 R9의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴아민기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.Ar 1 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron of Ar 5 to R 1 to R 9 Group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenes group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, an aryloxy group of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60, alkyloxy group of C 1 ~ C 40 of the , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group , C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group When substituted or unsubstituted with one or more selected substituents and substituted with a plurality of substituents, they are the same or different from each other.
이하, 본 발명을 상세히 설명한다.Hereinafter, the present invention will be described in detail.
1. 신규 유기 화합물1. New Organic Compounds
본 발명의 신규 화합물은 하기 화학식 1로 표시될 수 있다:The novel compounds of the present invention can be represented by the following formula (1):
[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,
*R1과 R2, R2와 R3, R3와 R4, R5와 R6, R6과 R7 및 R7과 R8 중 적어도 하나는 하기 화학식 2 내지 4 중 어느 하나로 표시되는 고리와 축합되어 축합 고리를 형성하고, 상기 R1과 R2, R2와 R3, R3와 R4, R4와 R5, R5와 R6, R6과 R7, R7과 R8 중 2 이상이 하기 화학식 2 내지 4로 표시되는 고리와 축합되는 경우, 각각 축합되는 고리는 동일하거나 상이하며;* R 1 and R 2, R 2 and R 3, R 3 and R 4, R 5 and R 6, R 6 and R 7, and R 7 and R 8 of the at least one represented by any one of following formulas 2 to 4 Condensed with a ring to form a condensed ring, wherein R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 4 and R 5 , R 5 and R 6 , R 6 and R 7 , R 7 and When two or more of R 8 are condensed with a ring represented by the following Chemical Formulas 2 to 4, the condensed rings are the same or different;
[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
상기 화학식 1 내지 4에서, In Chemical Formulas 1 to 4,
점선은 축합이 이루어지는 부분이며;The dotted line is the part where condensation takes place;
X1 내지 X3는 각각 독립적으로 O, S, N(Ar1), C(Ar2)(Ar3) 및 Si(Ar4)(Ar5)로 구성된 군으로부터 선택되나, X1 내지 X3 중 적어도 하나는 N(Ar1)이고;X 1 to X 3 are each independently selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), but X 1 to X 3 At least one of is N (Ar 1 );
Y1 내지 Y6은 각각 독립적으로 N 또는 C(R9)이며;Y 1 to Y 6 are each independently N or C (R 9 );
Ar1
내지 Ar5는 각각 독립적으로 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접한 기와 결합하여 축합 고리를 형성할 수 있고;Ar 1 Ar 5 is each independently C 1 ~ C 40 Alkyl group, C 2 ~ C 40 Alkenyl group, C 2 ~ C 40 Alkynyl group, C 3 ~ C 40 Cycloalkyl group, 3 to 40 heteroatoms Cycloalkyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyl Of silyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 May be selected from the group consisting of mono or diarylphosphinyl groups and C 6 -C 60 arylamine groups, or can be combined with adjacent groups to form a condensed ring;
상기 화학식 2 내지 4로 표시되는 고리와 축합 고리를 형성하지 않는 R1 내지 R8와, R9는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R9가 복수 개인 경우 복수 개의 R9는 서로 동일하거나 상이하며; R 1 to R 8 and R 9 which do not form a condensed ring with the ring represented by Formula 2 to 4, and R 9 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group of C 1 to C 40 , C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 To 60 heteroaryl groups, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl Phosphinicosuccinic aryl group and a C 6 ~ C 60 amine group is selected from the group consisting of, wherein R 9, when a plurality of individual plurality of R 9 is the same as or different from each other;
상기 Ar1
내지 Ar5 및 R1 내지 R9의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴아민기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.Ar 1 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron of Ar 5 to R 1 to R 9 Group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenes group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, an aryloxy group of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60, alkyloxy group of C 1 ~ C 40 of the , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group , C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group When substituted or unsubstituted with one or more selected substituents and substituted with a plurality of substituents, they are the same or different from each other.
본 발명의 상기 화학식 1로 표시되는 화합물은 종래 유기 전계 발광 소자용 재료[예: 4,4-디카바졸릴비페닐 (이하, 'CBP'라 함)]보다 높은 분자량을 갖기 때문에, 유리전이온도가 높아 열적 안정성이 우수할 뿐만 아니라, 캐리어 수송능, 발광능 등이 우수하다. 따라서, 상기 화학식 1의 화합물을 유기 전계 발광 소자가 포함할 경우, 소자의 구동전압, 효율, 수명 등이 향상될 수 있다.Since the compound represented by Chemical Formula 1 of the present invention has a higher molecular weight than the conventional organic electroluminescent device material (for example, 4,4-dicarbazolyl biphenyl (hereinafter referred to as 'CBP')), the glass transition temperature It is high in not only excellent thermal stability but also excellent carrier transport ability, luminous ability, etc. Therefore, when the organic electroluminescent device includes the compound of Formula 1, the driving voltage, efficiency, lifespan, etc. of the device may be improved.
일반적으로 유기 전계 발광 소자의 인광 발광층에서, 호스트 물질은 이의 삼중항 에너지 갭이 도펀트의 삼중항 에너지 갭보다 높아야 한다. 즉, 호스트의 가장 낮은 여기 상태가 도펀트의 가장 낮은 방출 상태보다 에너지가 더 높은 경우, 인광 발광 효율이 향상될 수 있다. 상기 화학식 1의 화합물은 삼중항 에너지가 높은 기본 골격에 특정의 치환기가 도입됨으로써, 에너지 준위가 도펀트보다 높게 조절될 수 있어 인광 호스트 물질로 사용될 수 있다.In general, in the phosphorescent layer of an organic electroluminescent device, the host material should have a triplet energy gap of which is higher than the triplet energy gap of the dopant. That is, when the lowest excited state of the host is higher in energy than the lowest emitted state of the dopant, phosphorescence efficiency may be improved. The compound of Formula 1 may be used as a phosphorescent host material by introducing a specific substituent into the basic skeleton having a triplet energy, the energy level can be adjusted higher than the dopant.
또한, 상기 화학식 1의 화합물은 상기 기본 골격에 도입되는 치환기의 종류에 따라 HOMO 및 LUMO 에너지 레벨을 조절할 수 있어, 넓은 밴드갭을 가질 수 있고, 높은 캐리어 수송성을 가질 수 있다. 예를 들어, 상기 화합물은 상기 기본 골격에 질소-함유 헤테로환(예컨대, 피리딘기, 피리미딘기, 트리아진기등)과 같이 전자 흡수성이 큰 전자 끌개기(EWG)가 결합될 경우, 분자 전체가 양극성의(bipolar) 특성을 갖기 때문에, 정공과 전자의 결합력을 높일 수 있다. 이와 같이, 상기 기본 골격에 EWG가 도입된 상기 화학식 1의 화합물은 우수한 캐리어 수송성 및 발광 특성이 우수하기 때문에, 유기 전계 발광 소자의 발광층 재료 이외, 전자주입/수송층 재료, 또는 수명 개선층 재료로도 사용될 수 있다. 한편, 상기 화학식 1의 화합물이 상기 기본 골격에 아릴아민기, 카바졸기, 터페닐기, 트리페닐렌기 등과 같이 전자 공여성이 큰 전자 주게기(EDG)가 결합될 경우, 정공의 주입 및 수송이 원활하게 이루어지기 때문에, 발광층 재료 이외, 정공주입/수송층 또는 발광 보조층 재료로도 유용하게 사용될 수 있다.In addition, the compound of Formula 1 may adjust HOMO and LUMO energy levels according to the type of substituents introduced into the basic skeleton, may have a wide bandgap, it may have a high carrier transport. For example, when the compound is bonded to an electron-withdrawing electron (EWG) having a high electron absorption such as a nitrogen-containing heterocycle (eg, pyridine group, pyrimidine group, triazine group, etc.) to the basic skeleton, Since it has a bipolar characteristic, it is possible to increase the bonding force between the hole and the electron. As such, the compound of Formula 1 having EWG introduced into the basic skeleton has excellent carrier transport properties and luminescent properties, and thus, as an electron injection / transport layer material or a life improvement layer material, in addition to the light emitting layer material of the organic EL device. Can be used. On the other hand, when the compound of Formula 1 is combined with an electron donor group (EDG) having a large electron donor such as an arylamine group, carbazole group, terphenyl group, triphenylene group, etc., the hole injection and transport is smooth. In addition to the light emitting layer material, it can be usefully used as a hole injection / transport layer or a light emitting auxiliary layer material.
이와 같이, 상기 화학식 1로 표시되는 화합물은 유기 전계 발광 소자의 발광 특성을 향상시킴과 동시에, 정공 주입/수송 능력, 전자 주입/수송 능력, 발광 효율, 구동 전압, 수명 특성 등을 향상시킬 수 있다. 따라서, 본 발명에 따른 화학식 1의 화합물은 유기 전계 발광 소자의 유기물층 재료, 바람직하게는 발광층 재료(녹색 및/또는 적색의 인광 호스트 재료), 전자 수송/주입층 재료 및 정공 수송/주입층 재료, 발광보조층 재료, 수명개선층 재료, 더 바람직하게는 발광층 재료, 전자 주입층 재료, 발광보조층 재료, 수명 개선층 재료로 사용될 수 있다.As described above, the compound represented by Chemical Formula 1 may improve the light emission characteristics of the organic EL device, and may also improve the hole injection / transport ability, the electron injection / transport capability, the luminous efficiency, the driving voltage, and the lifespan characteristics. . Accordingly, the compound of formula 1 according to the present invention is an organic material layer material of the organic electroluminescent device, preferably a light emitting layer material (green and / or red phosphorescent host material), electron transport / injection layer material and hole transport / injection layer material, It can be used as the light emitting auxiliary layer material, life improvement layer material, more preferably light emitting layer material, electron injection layer material, light emitting auxiliary layer material, life improving layer material.
또한, 상기 화학식 1의 화합물은 상기 기본 골격에 다양한 치환기, 특히 아릴기 및/또는 헤테로아릴기가 도입되어 화합물의 분자량이 유의적으로 증대됨으로써, 유리 전이온도가 향상될 수 있고, 이로 인해 종래의 발광 재료(예를 들어, CBP)보다 높은 열적 안정성을 가질 수 있다. 또한, 상기 화학식 1로 표시되는 화합물은 유기물층의 결정화 억제에도 효과가 있다. 따라서, 본 발명에 따른 화학식 1의 화합물을 포함하는 유기 전계 발광 소자는 성능 및 수명 특성이 크게 향상될 수 있고, 이러한 유기 전계 발광 소자가 적용된 풀 칼라 유기 발광 패널도 성능이 극대화될 수 있다.In addition, the compound of Formula 1 has a variety of substituents, especially aryl groups and / or heteroaryl groups introduced into the basic skeleton significantly increases the molecular weight of the compound, thereby improving the glass transition temperature, thereby conventional light emission It may have a higher thermal stability than the material (eg CBP). In addition, the compound represented by the formula (1) is effective in suppressing the crystallization of the organic material layer. Therefore, the organic electroluminescent device including the compound of Formula 1 according to the present invention can greatly improve performance and lifespan characteristics, and the full-color organic light emitting panel to which the organic electroluminescent device is applied can also maximize its performance.
본 발명의 바람직한 한 구현 예에 따르면, 상기 화합물은 하기 화학식 A-1 내지 A-9 중 어느 하나로 표시되는 화합물일 수 있다:According to one preferred embodiment of the present invention, the compound may be a compound represented by any one of the following Formulas A-1 to A-9:
상기 화학식 A-1 내지 A-9에서,In Chemical Formulas A-1 to A-9,
X1 내지 X3, R1 내지 R6, R8 및 Y1 내지 Y6 각각은 상기 화학식 1 내지 4에서 정의된 바와 같다. X 1 to X 3 , R 1 to R 6 , R 8 and Y 1 to Y 6 are each as defined in Chemical Formulas 1 to 4 above.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R1 내지 R9 및 Ar1
내지 Ar5 중 적어도 하나는 하기 화학식 5로 표시되는 치환기이며, 여기서 상기 R1 내지 R9 및 Ar1
내지 Ar5는 서로 동일하거나 상이할 수 있다:According to a preferred embodiment of the present invention, the R 1 to R 9 and Ar 1 To at least one of Ar 5 is a substituent represented by the following formula (5), wherein R 1 to R 9 and Ar 1 And Ar 5 may be the same or different from each other:
[화학식 5][Formula 5]
상기 화학식 5에서,In Chemical Formula 5,
**는 결합되는 부분을 의미하고;** means the part to be combined;
L1 및 L2는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며; L 1 and L 2 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;
R10은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; R 10 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phospha A aryl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;
상기 L1 및 L2의 아릴렌기 및 헤테로아릴렌기와, 상기 R10의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.Wherein L 1 and the L 2 arylene group and a heteroarylene group, an alkyl group of the R 10, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl The amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 An alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C 6 to C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphanyl group, C 6 ~ C 60 Mono or diaryl phosphinyl group and C 6 ~ C 6 When unsubstituted or substituted with one or more substituents selected from the group consisting of 0 arylsilyl groups, they are the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 Ar1
및 R9 중 적어도 하나는 상기 화학식 5로 표시되는 치환기일 수 있으며, 이 경우 상기 Ar1
및 R9는 서로 동일하거나 상이할 수 있다. 보다 바람직하게는 상기 Ar1은 상기 화학식 5로 표시되는 치환기일 수 있다. According to a preferred embodiment of the present invention, Ar 1 And at least one of R 9 may be a substituent represented by Formula 5, in which case Ar 1 And R 9 may be the same or different from one another. More preferably, Ar 1 may be a substituent represented by Formula 5.
본 발명의 바람직한 한 구현 예에 따르면, 상기 L1 및 L2는 각각 독립적으로 단일결합이거나 하기 화학식 B-1 내지 B-6 중 어느 하나로 표시되는 링커인 것이 발광 효율 및 구동 전압 특성에서 바람직하다:According to one preferred embodiment of the present invention, L 1 and L 2 are each independently a single bond or a linker represented by any one of the following formulas B-1 to B-6 is preferable in the luminous efficiency and driving voltage characteristics:
상기 화학식 B-1 내지 B-6에서,In Chemical Formulas B-1 to B-6,
*는 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
X4 및 X5은 각각 독립적으로 O, S, N(Ar6) 또는 C(Ar7)(Ar8)이며;X 4 and X 5 are each independently O, S, N (Ar 6 ) or C (Ar 7 ) (Ar 8 );
X6는 N 또는 C(Ar9)이며;X 6 is N or C (Ar 9 );
p는 0 내지 4의 정수이며;p is an integer from 0 to 4;
R11은 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R11이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 11 is heavy hydrogen, a halogen, a cyano group, a nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, a cycloalkyl group of C 2 ~ C 40 alkynyl group, C 3 ~ C 40 of nuclear atoms 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C An alkylsilyl group of 3 to C 40 , an arylsilyl group of C 6 to C 60 , an alkyl boron group of C 1 to C 40, an aryl boron group of C 6 to C 60 , an arylphosphanyl group of C 6 to C 60 , A C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylamine group may be selected from the group consisting of or adjacent to a condensed ring to form a condensed ring, when there are a plurality of R 11 They are mutually Same or different;
Ar6 내지 Ar9는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고;Ar 6 to Ar 9 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, selected from the group consisting arylsilyl a C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of, or by combining tile adjacent to which they are attached may form a condensed ring;
상기 R11 및 Ar6 내지 Ar9의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.Alkyl group of said R 11, and Ar 6 to Ar 9, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boronic Group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenes group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, an aryloxy group of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60, alkyloxy group of C 1 ~ C 40 of the , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group , the group consisting of C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 aryl group in the silyl When substituted with at least one selected more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R10은 수소, C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 10 is hydrogen, an alkyl group of C 1 ~ C 40 , an aryl group of C 6 ~ C 60 , a heteroaryl group of 5 to 60 nuclear atoms and C 6 ~ C 60 It may be selected from the group consisting of arylamine groups.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R10은 수소이거나 하기 화학식 C-1 내지 C-7 중 어느 하나로 표시되는 치환기인 것이 발광 효율 및 구동 전압 특성에서 바람직하다:According to a preferred embodiment of the present invention, the R 10 is hydrogen or a substituent represented by any one of the following formulas C-1 to C-7 is preferable in the luminous efficiency and driving voltage characteristics:
상기 화학식 C-1 내지 C-7에서,In Chemical Formulas C-1 to C-7,
*는 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
Z1 내지 Z5는 각각 독립적으로 N 또는 C(R16)이며;Z 1 to Z 5 are each independently N or C (R 16);
T1 및 T2는 각각 독립적으로 단일결합, C(R17)(R18), N(R19), O 및 S로 이루어진 군에서 선택되나, T1 및 T2 모두가 단일결합은 아니며;T 1 and T 2 are each independently selected from the group consisting of a single bond, C (R 17 ) (R 18 ), N (R 19 ), O and S, but not both T 1 and T 2 are single bonds;
q 및 r은 각각 독립적으로 0 내지 4의 정수이며;q and r are each independently integers of 0 to 4;
R12 및 R13은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R12 및 R13 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 12 and R 13 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of C 6 ~ C 60, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 An arylphosphanyl group, a C 6 ~ C 60 mono or diaryl phosphinyl group and a C 6 ~ C 60 arylsilyl group, or may be combined with an adjacent group to form a condensed ring, wherein R When 12 and R 13 are each plural, they are the same as or different from each other;
R14 내지 R19는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R16 내지 R19 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 14 to R 19 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ aryloxy C 60, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a nuclear atoms 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, selected from the group consisting of C 6 ~ C 60 mono or diaryl the Phosphinicosuccinic group and a C 6 ~ with an aryl silyl group of C 60, or combine tile adjacent to which they are attached may form a fused ring, When each of R 16 to R 19 plural is the same or different from each other;
상기 R12 내지 R19의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 
1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.Alkyl group of said R 12 to R 19, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 Aryl boron group of ~ C 60 , C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group Done When substituted or unsubstituted with one or more substituents and substituted with a plurality of substituents, they may be the same or different from each other.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R10은 상기 화학식 C-1 내지 C-5 중 어느 하나로 표시되는 치환기일 수 있다. According to a preferred embodiment of the present invention, R 10 may be a substituent represented by any one of Formulas C-1 to C-5.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R14 및 R15는 각각 독립적으로 수소, C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택될 수 있다.According to a preferred embodiment of the present invention, R 14 and R 15 are each independently hydrogen, an alkyl group of C 1 ~ C 40 , an aryl group of C 6 ~ C 60 , a heteroaryl group of 5 to 60 nuclear atoms and It may be selected from the group consisting of C 6 ~ C 60 arylamine group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R14 및 R15는 각각 독립적으로 페닐기, 비페닐기 및 나프탈레닐기로 이루어진 군에서 선택될 수 있다.According to one preferred embodiment of the present invention, R 14 and R 15 may be each independently selected from the group consisting of a phenyl group, a biphenyl group and a naphthalenyl group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R10은 하기 화학식 D-1 내지 D-24 중 어느 하나로 표시되는 치환기일 수 있다:According to one preferred embodiment of the present invention, R 10 may be a substituent represented by any one of the following Formulas D-1 to D-24:
상기 화학식 D-1 내지 D-24에서,In Chemical Formulas D-1 to D-24,
*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;
t는 0 내지 5의 정수이며,t is an integer from 0 to 5,
u는 0 내지 4의 정수이며;u is an integer from 0 to 4;
v는 0 내지 3의 정수이며;v is an integer from 0 to 3;
w는 0 내지 2의 정수이며;w is an integer from 0 to 2;
R20은 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R20이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 20 is deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, nuclear atom C 5 to C 60 aryloxy group, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 arylamine group, C 1 to C 40 alkylsilyl group, C 1 to C 40 alkyl boron group, C 6 to C 60 aryl boron group, C 6 to C 60 arylphosphanyl group, C 6 ~ mono or diaryl phosphine of C 60 blood group and a C 6 ~ C 60 selected from an aryl silyl group the group consisting of or of, by combining groups of adjacent, may form a fused ring, wherein R 20 is when multiple individual which Same or different from each other;
상기 R20의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있으며, The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group of R 20 , heterocycloalkyl group, arylamine group, alkylsilyl group, alkyl boron group, aryl boron group, Arylphosphanyl group, mono or diarylphosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 Arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 At least one member selected from the group consisting of an aryl boron group, a C 6 to C 60 arylphosphanyl group, a C 6 to C 60 mono or diaryl phosphinyl group, and a C 6 to C 60 arylsilyl group When unsubstituted or substituted with a substituent on the substituent, and substituted with a plurality of substituents, they may be the same as or different from each other,
R12, R13, R16 내지 R19, q 및 r 각각은 상기 화학식 C-1 내지 C-7에서 정의된 바와 같다.R 12 , R 13 , R 16 to R 19 , q and r are each as defined in Chemical Formulas C-1 to C-7.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R12, R13 및 R20은 각각 독립적으로 C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택될 수 있다.According to one embodiment, the preferred of the invention, the R 12, R 13 and R 20 are each independently a C 1 ~ C 40 alkyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group And it may be selected from the group consisting of C 6 ~ C 60 arylamine group.
본 발명의 바람직한 한 구현 예에 따르면, 상기 R12, R13 및 R20은 각각 독립적으로 페닐기, 비페닐기 및 나프탈레닐기로 이루어진 군에서 선택될 수 있다.According to one preferred embodiment of the present invention, R 12 , R 13 and R 20 may be each independently selected from the group consisting of a phenyl group, a biphenyl group and a naphthalenyl group.
본 발명의 화학식 1로 표시되는 화합물은 하기 화합물로 나타낼 수 있으나 이에 한정되는 것은 아니다: Compound represented by Formula 1 of the present invention may be represented by the following compounds, but is not limited thereto:
본 발명의 화학식 1의 화합물은 일반적인 합성방법에 따라 합성될 수 있다(Chem. Rev., 60:313 (1960); J.
Chem
. SOC. 4482 (1955); Chem. Rev. 95: 2457 (1995) 등 참조). 본 발명의 화합물에 대한 상세한 합성 과정은 후술하는 합성예에서 구체적으로 기술하도록 한다. Compounds of formula 1 of the present invention can be synthesized according to general synthetic methods ( Chem. Rev. , 60 : 313 (1960); J. Chem . SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995) ) And so on). Detailed synthesis procedures for the compounds of the present invention will be described in detail in the synthesis examples described below.
2. 유기 전계 발광 소자2. Organic electroluminescent device
한편, 본 발명의 다른 측면은 상기한 화학식 1로 표시되는 화합물을 포함하는 유기 전계 발광 소자를 제공한다.On the other hand, another aspect of the present invention provides an organic electroluminescent device comprising a compound represented by the formula (1).
구체적으로, 본 발명은 (i) 양극(anode), (ii) 음극(cathode) 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하며, 상기 유기물층 중 적어도 하나는 상기 화학식 1로 표시되는 화합물을 포함한다. 이때, 상기 화학식 1로 표시되는 화합물은 단독 또는 2종 이상이 혼합되어 사용될 수 있다.Specifically, the present invention includes (i) an anode, (ii) a cathode and (iii) at least one organic layer interposed between the anode and the cathode, wherein at least one of the organic layers is It includes a compound represented by the formula (1). In this case, the compound represented by Formula 1 may be used alone or two or more kinds are mixed.
본 발명의 일례에 따르면, 상기 1층 이상의 유기물층은 정공주입층, 정공수송층, 발광층, 전자수송층 및 전자주입층 중 어느 하나 이상을 포함할 수 있는데, 이 중에서 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.According to an embodiment of the present invention, the one or more organic material layers may include 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, wherein at least one organic material layer is represented by the formula (1) It may include a compound.
바람직하게는 상기 화학식 1로 표시되는 화합물이 포함되는 유기물층은 발광층 또는 정공 수송층일 수 있고, 더욱 바람직하게는, 상기 화학식 1로 표시되는 화합물이 발광층에 포함될 경우, 유기 전계 발광 소자의 발광효율, 휘도, 전력효율, 열적 안정성 및 소자 수명을 매우 향상시킬 수 있다.Preferably, the organic material layer including the compound represented by Formula 1 may be a light emitting layer or a hole transport layer, and more preferably, when the compound represented by Formula 1 is included in the light emitting layer, the luminous efficiency and luminance of the organic EL device It can greatly improve power efficiency, thermal stability and device life.
예를 들어, 상기 화학식 1로 표시되는 화합물은 발광층의 인광 호스트, 형광 호스트 또는 도펀트 재료일 수 있으며, 바람직하게는 발광층의 인광 호스트일 수 있다.For example, the compound represented by Chemical Formula 1 may be a phosphorescent host, a fluorescent host, or a dopant material of the light emitting layer, and preferably, a phosphorescent host of the light emitting layer.
본 발명의 다른 일례에 따르면, 상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광 보조층, 발광층, 전자 수송층 및 전자 주입층 중 어느 하나 이상을 포함할 수 있는데, 이때 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다.According to another example of the present invention, the one or more organic material layers may include any one or more of a hole injection layer, a hole transport layer, a light emitting auxiliary layer, a light emitting layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer is It may include a compound represented by the formula (1).
바람직하게는 상기 화학식 1로 표시되는 화합물이 포함되는 유기물층은 발광 보조층일 수 있다. 특히, 상기 화학식 1로 표시되는 화합물이 유기 전계 발광 소자의 발광 보조층 물질에 포함되는 경우, 유기 전계 발광 소자의 효율(발광 효율 및 전력 효율), 수명 및 휘도는 보다 향상시키고, 구동 전압은 더욱 낮출 수 있다.Preferably, the organic material layer including the compound represented by Chemical Formula 1 may be a light emission auxiliary layer. In particular, when the compound represented by Chemical Formula 1 is included in the light emitting auxiliary layer material of the organic light emitting diode, the efficiency (light emitting efficiency and power efficiency), lifetime, and luminance of the organic light emitting diode are further improved, and the driving voltage is further improved. Can be lowered.
본 발명의 또 다른 일례에 따르면, 상기 1층 이상의 유기물층은 정공 주입층, 정공 수송층, 발광층, 전자 수송 보조층, 전자 수송층 및 전자 주입층 중 어느 하나 이상을 포함할 수 있는데, 이때 적어도 하나의 유기물층은 상기 화학식 1로 표시되는 화합물을 포함할 수 있다. According to another example of the present invention, the one or more organic material layers may include any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport auxiliary layer, an electron transport layer and an electron injection layer, wherein at least one organic material layer May include a compound represented by Chemical Formula 1.
바람직하게는, 상기 화학식 1로 표시되는 화합물이 포함되는 유기물층은전자 수송 보조층일 수 있다. 특히 상기 화학식 1로 표시되는 화합물이 유기 전계 발광 소자의 전자수송보조층에 포함되는 경우, 유기 전계 발광 소자의 효율(발광 효율 및 전력 효율), 수명 및 휘도는 보다 향상시키고, 구동 전압은 더욱 낯출 수 있다.Preferably, the organic material layer including the compound represented by Formula 1 may be an electron transport auxiliary layer. In particular, when the compound represented by Formula 1 is included in the electron transport auxiliary layer of the organic electroluminescent device, the efficiency (light emitting efficiency and power efficiency), lifespan and luminance of the organic electroluminescent device are further improved, and the driving voltage is more fragile. Can be.
이러한 본 발명의 유기 전계 발광 소자의 구조는 특별히 한정되지 않으며, 예컨대 기판 위에, 양극, 1층 이상의 유기물층 및 음극이 순차적으로 적층될 뿐만 아니라, 전극과 유기물층 계면에 절연층 또는 접착층이 삽입된 구조일 수 있다.The structure of the organic EL device of the present invention is not particularly limited, and for example, the anode, one or more organic material layers and the cathode are sequentially stacked on the substrate, and an insulating layer or an adhesive layer is inserted at the interface between the electrode and the organic material layer. Can be.
일례에 따르면, 상기 유기 전계 발광 소자는 기판 위에, 양극, 정공 주입층, 정공 수송층, 발광층, 전자 수송층 및 음극이 순차적으로 적층된 구조일 수 있고, 필요에 따라서는, 상기 정공 수송층과 발광층 사이에는 발광 보조층이 삽입될 수 있으며 또, 상기 전자 수송층 위에는 전자 주입층이 위치할 수도 있다.According to an example, the organic EL device may have a structure in which an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked on a substrate, and, if necessary, between the hole transport layer and the light emitting layer. An emission auxiliary layer may be inserted, and an electron injection layer may be positioned on the electron transport layer.
본 발명의 유기 전계 발광 소자는 상기 1층 이상의 유기물층 중에서 적어도 하나로, 예컨대, 발광층 또는 발광 보조층은 상기 화학식 1로 표시되는 화합물을 포함하도록 형성하는 것을 제외하고는, 당 기술 분야에 알려져 있는 재료 및 방법을 이용하여 유기물층 및 전극을 형성함으로써 제조될 수 있다.The organic electroluminescent device of the present invention is at least one of the one or more organic material layers, for example, a light emitting layer or a light emitting auxiliary layer is formed so as to include a compound represented by the formula (1), and materials known in the art It can be prepared by forming an organic material layer and an electrode using a method.
상기 유기물층은 진공증착법이나 용액 도포법에 의하여 형성될 수 있다. 상기 용액 도포법의 예로는 스핀 코팅, 딥코팅, 닥터 블레이딩, 잉크젯 프린팅 또는 열 전사법 등이 있으나, 이들에 한정되지는 않는다.The organic material layer may be formed by a vacuum deposition method or a solution coating method. Examples of the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
본 발명에서 유기 전계 발광 소자의 제조 시 사용 가능한 기판의 예로는 실리콘 웨이퍼, 석영 또는 유리판, 금속판, 플라스틱 필름이나 시트 등이 있는데, 이에 한정되지 않는다.Examples of the substrate that can be used in the manufacture of the organic EL device in the present invention include a silicon wafer, quartz or glass plate, a metal plate, a plastic film or sheet, but is not limited thereto.
또한, 양극 물질의 예로는 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 및 폴리아닐린과 같은 전도성 고분자; 또는 카본블랙 등이 있으나, 이들에 한정되는 것은 아니다.Further, examples of the anode material include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole and polyaniline; Or carbon black, but is not limited thereto.
또한, 음극 물질의 예로는 마그네슘, 칼슘, 나트륨, 칼륨, 타이타늄, 인듐, 이트륨, 리튬, 가돌리늄, 알루미늄, 은, 주석, 또는 납과 같은 금속 또는 이들의 합금; LiF/Al 또는 LiO2/Al과 같은 다층 구조 물질 등이 있으나, 이에 한정되는 것은 아니다.Further, examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
또한, 정공 주입층, 정공 수송층, 전자 주입층 및 전자 수송층으로 사용되는 물질은 특별히 한정되는 것은 아니며, 당업계에 알려진 통상의 물질이라면 제한없이 사용할 수 있다.In addition, the material used as the hole injection layer, the hole transport layer, the electron injection layer and the electron transport layer is not particularly limited, and any material known in the art may be used without limitation.
이하 본 발명을 실시예를 통하여 상세히 설명하나, 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 Examples, but the following Examples are merely illustrative of the present invention, and the present invention is not limited by the following Examples.
[[
준비예Preparation
1] 화합물 1] Compound
Inv1Inv1
및 And
Inv2의Inv2
합성 synthesis
<단계 1> 2-( e디벤조[b,e][1,4]디옥신 -2-일)-4,4,5,5- 테트라메틸 -1,3,2- 디옥사보로란의 합성 <Step 1> 2- ( eDibenzo [b, e] [1,4] dioxine -2-yl) -4,4,5,5- tetramethyl- 1,3,2 - diox of sabororane synthesis
2-브로모디벤조[b,e][1,4]디옥신 (100g, 0.38mol), 4,4,4',4',5,5,5',5'-옥타메틸-2,2'-비(1,3,2-디옥사보로란) (115.8g, 0.46mol), Pd(dppf)Cl2 (31g, 0.038mol) 및 KOAc(111.9g, 1.14mol)을 플라스크에 넣은 다음, 여기에 1,4-디옥산 (2L)를 넣어 녹인 후, 8시간 동안 가열 교반하였다. 반응 종료 후, 증류수를 넣고 에틸아세테이트로 유기층을 추출하였다. 얻은 유기층을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 2-(디벤조[b,e][1,4]디옥신-2-일)-4,4,5,5-테트라메틸-1,3,2-디옥사보로란 (73g, 수율 62%)을 얻었다. 2-bromodibenzo [b, e] [1,4] dioxine (100 g, 0.38 mol), 4,4,4 ', 4', 5,5,5 ', 5'-octamethyl-2,2 '-Ratio (1,3,2-dioxaborolane) (115.8 g, 0.46 mol), Pd (dppf) Cl 2 (31 g, 0.038 mol) and KOAc (111.9 g, 1.14 mol) were added to the flask 1,4-dioxane (2L) was added and dissolved therein, followed by heating and stirring for 8 hours. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to give compound 2- (dibenzo [b, e] [1,4] dioxin-2-yl) -4,4,5 , 5-tetramethyl-1,3,2-dioxaborolane (73 g, yield 62%) was obtained.
<단계 2> 2-<Step 2> 2-
(2-니트로나프탈렌-1-일)디벤조[b,e](2-nitronaphthalen-1-yl) dibenzo [b, e]
[1,[One,
4]디옥신의4] of dioxin
합성 synthesis
상기 <단계 1>에서 얻은 2-(디벤조[b,e][1,4]디옥신-2-일)-4,4,5,5-테트라메틸-1,3,2-디옥사보로란 (73g, 0.235mol), 1-브로모-2-니트로나프탈렌 (71g, 0.282mol) 및 Pd(PPh3)4 (13.5g, 0.011mol)을 플라스크에 넣고, 여기에 2M Na2CO3 포화 수용액 (352㎖)과 1,4-디옥산 (2L)을 넣어 녹인 후, 8시간 동안 가열 교반하였다. 반응 종료 후, 증류수를 넣고 에틸아세테이트로 유기층을 추출하였다. 얻은 유기층을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 2-(2-니트로나프탈렌-1-일)디벤조[b,e][1,4]디옥신 (75g, 수율 91%)을 얻었다.2- (dibenzo [b, e] [1,4] dioxin-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxabo obtained in the above <Step 1> Loran (73g, 0.235mol), 1-bromo-2-nitronaphthalene (71g, 0.282mol) and Pd (PPh 3 ) 4 (13.5g, 0.011mol) are placed in a flask, which is 2M Na 2 CO 3 Saturated aqueous solution (352 ml) and 1,4-dioxane (2 L) were added and dissolved, and the mixture was heated and stirred for 8 hours. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The resulting organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to give compound 2- (2-nitronaphthalen-1-yl) dibenzo [b, e] [1,4] dioxine (75 g , Yield 91%) was obtained.
<단계 3> 화합물 <Step 3> Compound
Inv1Inv1
, 및 , And
Inv2의Inv2
합성 synthesis
질소 기류 하에서 상기 <단계 2>에서 얻은 2-(2-니트로나프탈렌-1-일)디벤조[b,e][1,4]디옥신 (75g, 0.212mol), PPh3 (67g, 0.255mol), 및 1,2-디클로로벤젠 (1L)을 혼합한 후, 12시간 동안 교반하였다. 반응 종료 후, 1,2-디클로로벤젠을 제거하고, 디클로로메탄으로 유기층을 추출하였다. 얻은 유기층을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 Inv1(40g, 수율 58 %), 및 화합물 Inv2 (12 g, 수율 17 %)을 획득하였다.2- (2-nitronaphthalen-1-yl) dibenzo [b, e] [1,4] dioxine (75 g, 0.212 mol) obtained in the above <Step 2> under a nitrogen stream, PPh 3 (67 g, 0.255 mol) ), And 1,2-dichlorobenzene (1 L) were mixed and then stirred for 12 hours. After the reaction was completed, 1,2-dichlorobenzene was removed, and the organic layer was extracted with dichloromethane. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to obtain Compound Inv1 (40 g, yield 58%), and Compound Inv2 (12 g, yield 17%).
[[
준비예Preparation
2] 화합물 2] compound
Inv3Inv3
및 And
Inv4의Inv4
합성 synthesis
상기 준비예 1과 동일한 과정을 수행하되, <단계 2>에서 1-브로모-2-니트로나프탈렌 대신 2-브로모-3-니트로나프탈렌을 사용하여 화합물 Inv3(34.2g, 수율 50 %), 및 화합물 Inv4 (17.1 g, 수율 25 %)을 수득 하였다 The same procedure as in Preparation Example 1 was carried out, except that <bromo-2-nitronaphthalene was used instead of 1-bromo-2-nitronaphthalene in compound Inv3 (34.2 g, yield 50%), and Compound Inv4 (17.1 g, Yield 25%) was obtained.
[[
준비예Preparation
3] 화합물 3] compound
Inv5Inv5
및 And
Inv6의Inv6
합성 synthesis
상기 준비예 1과 동일한 과정을 수행하되, <단계 2>에서 1-브로모-2-니트로나프탈렌 대신 2-브로모-1-니트로나프탈렌을 사용하여 화합물 Inv5(20.5g, 수율 30 %), 및 화합물 Inv6 (27.4 g, 수율 40 %)을 수득 하였다 The same procedure as in Preparation Example 1 was carried out, except that <bromo-2-nitronaphthalene was used instead of 1-bromo-2-nitronaphthalene in compound Inv5 (20.5 g, yield 30%), and Compound Inv6 (27.4 g, yield 40%) was obtained.
[[
준비예Preparation
4] 화합물 4] compound
Inv7Inv7
및 And
Inv8의Inv8
합성 synthesis
<단계 1> 2-(2-니트로나프탈렌-1-일)<Step 1> 2- (2-nitronaphthalen-1-yl)
싸이안트렌의Psychedelic
합성 synthesis
2-(디벤조[b,e][1,4]디옥신-2-일)-4,4,5,5-테트라메틸-1,3,2-디옥사보로란 (100g, 0.384mol), 1-브로모-2-니트로나프탈렌 (106g, 0.422mol) 및 Pd(PPh3)4 (13.3g, 11.5mmol)을 플라스크에 넣고, 여기에 2M Na2CO3 포화 수용액 (576㎖)과 1,4-디옥산 (2L)을 넣어 녹인 후, 8시간 동안 가열 교반하였다. 반응 종료 후, 증류수를 넣고 에틸아세테이트로 유기층을 추출하였다. 얻은 유기층을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 2-(2-니트로나프탈렌-1-일)싸이안트렌 (128g, 수율 86%)을 얻었다.2- (dibenzo [b, e] [1,4] dioxin-2-yl) -4,4,5,5-tetramethyl-1,3,2-dioxaborolane (100 g, 0.384 mol ), 1-bromo-2-nitronaphthalene (106 g, 0.422 mol) and Pd (PPh 3 ) 4 (13.3 g, 11.5 mmol) were added to the flask, and a saturated aqueous solution of 2M Na 2 CO 3 (576 mL) 1,4-dioxane (2L) was added to dissolve and then heated and stirred for 8 hours. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na 2 S0 4 , distilled under reduced pressure, and then purified by column chromatography to obtain compound 2- (2-nitronaphthalen-1-yl) thiarene (128g, yield 86%).
<단계 2> 화합물 <Step 2> Compound
Inv1Inv1
, 및 , And
Inv2의Inv2
합성 synthesis
질소 기류 하에서 상기 <단계 1>에서 얻은 2-(2-니트로나프탈렌-1-일)싸이안트렌 (128g, 0.330mol), PPh3 (216g, 0.825mol), 및 1,2-디클로로벤젠 (2L)을 혼합한 후, 12시간 동안 교반하였다. 반응 종료 후, 1,2-디클로로벤젠을 제거하고, 디클로로메탄으로 유기층을 추출하였다. 얻은 유기층을 Na2SO4로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 Inv7(72.7g, 수율 62 %), 및 화합물 Inv8 (24.5 g, 수율 21 %)을 획득하였다.2- (2-nitronaphthalen-l-yl) thianthrene (128g, 0.330mol), PPh 3 (216g, 0.825mol), and 1,2-dichlorobenzene (2L) obtained in <Step 1> under nitrogen stream ) Was mixed and stirred for 12 hours. After the reaction was completed, 1,2-dichlorobenzene was removed, and the organic layer was extracted with dichloromethane. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to obtain Compound Inv7 (72.7 g, yield 62%), and Compound Inv8 (24.5 g, yield 21%).
[[
준비예Preparation
5] 화합물 5] compound
Inv9Inv9
및 And
Inv10의Inv10
합성 synthesis
상기 준비예 4과 동일한 과정을 수행하되, <단계 1>에서 1-브로모-2-니트로나프탈렌 대신 2-브로모-3-니트로나프탈렌을 사용하여 화합물 Inv9(52.6g, 수율 45 %), 및 화합물 Inv12 (35.1 g, 수율 30 %)을 수득 하였다 The same procedure as in Preparation Example 4 was carried out, except for using Compound 1 (Bromo-3-nitronaphthalene instead of 1-bromo-2-nitronaphthalene in <Step 1> Compound Inv9 (52.6g, 45% yield), and Compound Inv12 (35.1 g, Yield 30%) was obtained.
[[
준비예Preparation
6] 화합물 6] compound
Inv11Inv11
및 And
Inv12의Inv12
합성 synthesis
상기 준비예 4과 동일한 과정을 수행하되, <단계 1>에서 1-브로모-2-니트로나프탈렌 대신 2-브로모-1-니트로나프탈렌을 사용하여 화합물 Inv11(35.1g, 수율 30 %), 및 화합물 Inv12 (46.8 g, 수율 40 %)을 수득 하였다 The same procedure as in Preparation Example 4 was carried out, except that <bromo-2-nitronaphthalene was used instead of 1-bromo-2-nitronaphthalene in a compound Inv11 (35.1 g, 30% yield), and Compound Inv12 (46.8 g, yield 40%) was obtained
[[
반응예Example of reaction
1] One]
CpdCpd
4의 합성 4, composite
준비예 1에서 합성된 화합물 Inv 2 (3.2 g, 10.0 mmol), 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 (4.6 g, 12.0 mmol)을 톨루엔 100 ㎖에 녹인 다음, Pd2(dba)3 (0.9g, 1.0mmol)을 질소 하에서 투입하였다. 이후, 여기에 NaOtBu (2.9g, 30 mmol)을 넣은 후, (t-Bu)3P (1.0 ㎖, 1.0mmol)을 상기 반응액에 투입한 다음, 혼합물을 5시간 동안 환류 교반하였다. Compound Inv 2 (3.2 g, 10.0 mmol) and 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine (4.6 g, 12.0 mmol) synthesized in Preparation Example 1 were prepared. After dissolving in 100 ml of toluene, Pd 2 (dba) 3 (0.9 g, 1.0 mmol) was added under nitrogen. Thereafter, NaOtBu (2.9 g, 30 mmol) was added thereto, and (t-Bu) 3 P (1.0 mL, 1.0 mmol) was added to the reaction solution, and the mixture was stirred under reflux for 5 hours.
TLC로 반응이 종결되는 것을 확인한 후, 상온으로 식혔다. 반응 종료 후, 증류수를 넣고 에틸아세테이트로 유기층을 추출하였다. 얻어진 유기층을 Na2SO4 로 건조시키고 감압 증류한 다음, 컬럼 크로마토그래피로 정제하여 화합물 Cpd 4 (6.2g, 수율 89%)을 얻었다. After confirming that the reaction was terminated by TLC, it was cooled to room temperature. After the reaction was completed, distilled water was added and the organic layer was extracted with ethyl acetate. The obtained organic layer was dried over Na 2 SO 4 , distilled under reduced pressure, and purified by column chromatography to obtain compound Cpd 4 (6.2 g, yield 89%).
HRMS [M]+: 630.206HRMS [M] + : 630.206
[[
반응예Example of reaction
2] 2]
CpdCpd
19의 합성 19 Synthesis
준비예 1에서 합성된 화합물 Inv 2 (10 g, 30.9 mmol), NaH(40%) (2.2 g, 37.1 mmol)을 톨루엔 DMF 150㎖에 녹인 다음, 1시간 동안 상온에서 교반 한 후 2-클로로-4-페닐퀴나졸린 (7.8 g, 32.4 mmol)을 질소 하에서 상기 반응액에 투입한 다음, 혼합물을 12시간 동안 교반하였다. Compound Inv 2 (10 g, 30.9 mmol) and NaH (40%) (2.2 g, 37.1 mmol) synthesized in Preparation Example 1 were dissolved in 150 ml of toluene DMF, and then stirred at room temperature for 1 hour, followed by 2-chloro- 4-phenylquinazoline (7.8 g, 32.4 mmol) was added to the reaction solution under nitrogen, and the mixture was stirred for 12 hours.
TLC로 반응이 종결되는 것을 확인한 후. 생성된 물질을 필터 하고 EtOH로 세척하여 화합물 Cpd 19 (12.0g, 수율 74%)을 얻었다. After confirming the reaction was terminated by TLC. The resulting material was filtered and washed with EtOH to give compound Cpd 19 (12.0 g, 74% yield).
HRMS [M]+: 527.163HRMS [M] + : 527.163
[[
반응예Example of reaction
3] 3]
CpdCpd
10의 합성 10 composite
상기 반응예 1과 동일한 과정을 수행하되, 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-(3'-브로모-[1,1'-바이페닐]-3-일)-4,6-다이페닐-1,3,5-트리아진을 사용하여 화합물 Cpd 10 (7.8g, 수율 90%)을 얻었다. The same process as in Example 1 was carried out, but instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, 2- (3'-bromo- [1,1 Compound Cpd 10 (7.8 g, 90% yield) was obtained using '-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine.
HRMS [M]+: 706.237HRMS [M] + : 706.237
[[
반응예Example of reaction
4] 4]
CpdCpd
11의 합성 11, synthesis
상기 반응예 1과 동일한 과정을 수행하되, 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-(4'-브로모-[1,1'-바이페닐]-3-일)-4,6-다이페닐-1,3,5-트리아진을 사용하여 화합물 Cpd 11 (6.1g, 수율 87%)을 얻었다. The same process as in Example 1 was carried out, but instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, 2- (4'-bromo- [1,1 Compound Cpd 11 (6.1 g, yield 87%) was obtained using '-biphenyl] -3-yl) -4,6-diphenyl-1,3,5-triazine.
HRMS [M]+: 706.237HRMS [M] + : 706.237
[[
반응예Example of reaction
5] 5]
CpdCpd
24의 합성 24 composites
상기 반응예 1과 동일한 과정을 수행하되, 2-(3-브로모페닐)-4,6-디페닐-1,3,5-트리아진 대신 2-(3'-브로모-[1,1'-바이페닐]-3-일)-4-페닐퀴나졸린을 사용하여 화합물 Cpd 24 (5.7g, 수율 84%)을 얻었다. The same process as in Example 1 was carried out, but instead of 2- (3-bromophenyl) -4,6-diphenyl-1,3,5-triazine, 2- (3'-bromo- [1,1 Compound Cpd 24 (5.7 g, yield 84%) was obtained using '-biphenyl] -3-yl) -4-phenylquinazolin.
HRMS [M]+: 679.226HRMS [M] + : 679.226
[[
합성예Synthesis Example
6] 6]
CpdCpd
28의 합성 28 Synthesis
상기 반응예 1과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 8을 사용하여 화합물 Cpd 28 (5.4g, 수율 82%)을 얻었다. Compound Cpd 28 (5.4 g, yield 82%) was obtained in the same manner as in Example 1 except that compound Inv 8 was used instead of compound Inv 2.
HRMS [M]+: 662.160HRMS [M] + : 662.160
[[
반응예Example of reaction
7] 7]
CpdCpd
34의 합성 Synthesis of 34
상기 반응예 3과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 8을 사용하여 화합물 Cpd 34 (6.0g, 수율 81%)을 얻었다. Compound Cpd 34 (6.0 g, Yield 81%) was obtained in the same manner as in Example 3, using Compound Inv 8 instead of Compound Inv 2.
HRMS [M]+: 738.191HRMS [M] + : 738.191
[[
반응예Example of reaction
8] 8]
CpdCpd
35의 합성 Synthesis of 35
상기 반응예 4과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 8을 사용하여 화합물 Cpd 35 (6.1g, 수율 83%)을 얻었다. Compound Cpd 35 (6.1 g, yield 83%) was obtained in the same manner as in Example 4, except that compound Inv 8 was used instead of compound Inv 2.
HRMS [M]+: 738.191HRMS [M] + : 738.191
[[
합성예Synthesis Example
9] 9]
CpdCpd
43의 합성 Synthesis of 43
상기 반응예 2과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 8을 사용하여 화합물 Cpd 43 (4.8g, 수율 87%)을 얻었다. Compound Cpd 43 (4.8 g, yield 87%) was obtained in the same manner as in Example 2 except that compound Inv 8 was used instead of compound Inv 2.
HRMS [M]+: 559.118HRMS [M] + : 559.118
[[
반응예Example of reaction
10] 10]
CpdCpd
48의 합성 48 composites
상기 반응예 5과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 8을 사용하여 화합물 Cpd 48 (6.0g, 수율 84%)을 얻었다. Compound Cpd 48 (6.0 g, yield 84%) was obtained in the same manner as in Example 5 except that compound Inv 8 was used instead of compound Inv 2.
HRMS [M]+: 711.180HRMS [M] + : 711.180
[[
합성예Synthesis Example
11] 11]
CpdCpd
52의 합성 52 composites
상기 반응예 1과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 4을 사용하여 화합물 Cpd 52 (6.2g, 수율 89%)을 얻었다. Compound Cpd 52 (6.2 g, yield 89%) was obtained in the same manner as in Example 1 except that compound Inv 4 was used instead of compound Inv 2.
HRMS [M]+: 630.206HRMS [M] + : 630.206
[[
반응예Example of reaction
12] 12]
CpdCpd
58의 합성 58 composites
상기 반응예 3과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 4을 사용하여 화합물 Cpd 58 (7.8g, 수율 90%)을 얻었다. Compound Cpd 58 (7.8 g, yield 90%) was obtained in the same manner as in Example 3, using Compound Inv 4 instead of Compound Inv 2.
HRMS [M]+: 706.237HRMS [M] + : 706.237
[[
반응예Example of reaction
13] 13]
CpdCpd
59의 합성 59 composites
상기 반응예 4과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 4을 사용하여 화합물 Cpd 59 (6.1g, 수율 87%)을 얻었다. Compound Cpd 59 (6.1 g, yield 87%) was obtained by following the same procedure as in Example 4, using Compound Inv 4 instead of Compound Inv 2.
HRMS [M]+: 706.237HRMS [M] + : 706.237
[[
합성예Synthesis Example
14] 14]
CpdCpd
67의 합성 Synthesis of 67
상기 반응예 2과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 4을 사용하여 화합물 Cpd 67 (12.0g, 수율 74%)을 얻었다. Compound Cpd 67 (12.0 g, yield 74%) was obtained by performing the same procedure as in Example 2, but using compound Inv 4 instead of compound Inv 2.
HRMS [M]+: 527.163HRMS [M] + : 527.163
[[
반응예Example of reaction
15] 15]
CpdCpd
72의 합성 72 composites
상기 반응예 5과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 4을 사용하여 화합물 Cpd 72 (5.7g, 수율 84%)을 얻었다. Compound Cpd 72 (5.7 g, yield 84%) was obtained in the same manner as in Example 5 except that compound Inv 4 was used instead of compound Inv 2.
HRMS [M]+: 679.226HRMS [M] + : 679.226
[[
합성예Synthesis Example
16] 16]
CpdCpd
76의 합성 76 Synthesis
상기 반응예 6과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 10을 사용하여 화합물 Cpd 76 (5.4g, 수율 82%)을 얻었다. Compound Cpd 76 (5.4 g, yield 82%) was obtained in the same manner as in Example 6 except that compound Inv 10 was used instead of compound Inv 8.
HRMS [M]+: 662.160HRMS [M] + : 662.160
[[
반응예Example of reaction
17] 17]
CpdCpd
82의 합성 Synthesis of 82
상기 반응예 7과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 10을 사용하여 화합물 Cpd 82 (6.0g, 수율 81%)을 얻었다. Compound Cpd 82 (6.0 g, yield 81%) was obtained in the same manner as in Example 7, except that compound Inv 10 was used instead of compound Inv 8.
HRMS [M]+: 738.191HRMS [M] + : 738.191
[[
반응예Example of reaction
18] 18]
CpdCpd
83의 합성 Synthesis of 83
상기 반응예 8과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 10을 사용하여 화합물 Cpd 83 (6.1g, 수율 83%)을 얻었다. Compound Cpd 83 (6.1 g, yield 83%) was obtained in the same manner as in Example 8 except that compound Inv 10 was used instead of compound Inv 8.
HRMS [M]+: 738.191HRMS [M] + : 738.191
[[
합성예Synthesis Example
19] 19]
CpdCpd
91의 합성 Synthesis of 91
상기 반응예 9과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 10을 사용하여 화합물 Cpd 91 (4.8g, 수율 87%)을 얻었다. Compound Cpd 91 (4.8 g, yield 87%) was obtained in the same manner as in Example 9, but using compound Inv 10 instead of compound Inv 8.
HRMS [M]+: 559.118HRMS [M] + : 559.118
[[
반응예Example of reaction
20] 20]
CpdCpd
96의 합성 96 composites
상기 반응예 10과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 10을 사용하여 화합물 Cpd 96 (6.0g, 수율 84%)을 얻었다. Compound Cpd 96 (6.0 g, yield 84%) was obtained in the same manner as in Example 10, but using compound Inv 10 instead of compound Inv 8.
HRMS [M]+: 711.180HRMS [M] + : 711.180
[[
합성예Synthesis Example
21] 21]
CpdCpd
100의 합성 100 synthetic
상기 반응예 1과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 5을 사용하여 화합물 Cpd 100 (6.2g, 수율 89%)을 얻었다. Compound Cpd 100 (6.2 g, yield 89%) was obtained in the same manner as in Example 1 except that compound Inv 5 was used instead of compound Inv 2.
HRMS [M]+: 630.206HRMS [M] + : 630.206
[[
반응예Example of reaction
22] 22]
CpdCpd
106의 합성 106 composites
상기 반응예 3과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 5을 사용하여 화합물 Cpd 106 (7.8g, 수율 90%)을 얻었다. Compound Cpd 106 (7.8 g, 90% yield) was obtained by performing the same procedure as in Example 3, using compound Inv 5 instead of compound Inv 2.
HRMS [M]+: 706.237HRMS [M] + : 706.237
[[
반응예Example of reaction
23] 23]
CpdCpd
107의 합성 107 Synthesis
상기 반응예 4과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 5을 사용하여 화합물 Cpd 107 (6.1g, 수율 87%)을 얻었다. Compound Cpd 107 (6.1 g, yield 87%) was obtained in the same manner as in Example 4 except using compound Inv 5 instead of compound Inv 2.
HRMS [M]+: 706.237HRMS [M] + : 706.237
[[
합성예Synthesis Example
24] 24]
CpdCpd
115의 합성 Synthesis of 115
*상기 반응예 2과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 5을 사용하여 화합물 Cpd 115 (12.0g, 수율 74%)을 얻었다. * Compound Cpd 115 (12.0 g, yield 74%) was obtained in the same manner as in Example 2, using Compound Inv 5 instead of Compound Inv 2.
HRMS [M]+: 527.163HRMS [M] + : 527.163
[[
반응예Example of reaction
25] 25]
CpdCpd
120의 합성 120 composites
상기 반응예 5과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 5을 사용하여 화합물 Cpd 120 (5.7g, 수율 84%)을 얻었다. Compound Cpd 120 (5.7 g, yield 84%) was obtained using the same procedure as in Example 5, but using compound Inv 5 instead of compound Inv 2.
HRMS [M]+: 679.226HRMS [M] + : 679.226
[[
합성예Synthesis Example
26] 26]
CpdCpd
124의 합성 Synthesis of 124
상기 반응예 6과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 11을 사용하여 화합물 Cpd 124 (5.4g, 수율 82%)을 얻었다. Compound Cpd 124 (5.4 g, yield 82%) was obtained in the same manner as in Example 6 except that compound Inv 11 was used instead of compound Inv 8.
HRMS [M]+: 662.160HRMS [M] + : 662.160
[[
반응예Example of reaction
27] 27]
CpdCpd
130의 합성 130 composites
상기 반응예 7과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 11을 사용하여 화합물 Cpd 130 (6.0g, 수율 81%)을 얻었다. Compound Cpd 130 (6.0 g, yield 81%) was obtained in the same manner as in Example 7, except that compound Inv 11 was used instead of compound Inv 8.
HRMS [M]+: 738.191HRMS [M] + : 738.191
[[
반응예Example of reaction
28] 28]
CpdCpd
131의 합성 Synthesis of 131
상기 반응예 8과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 11을 사용하여 화합물 Cpd 131 (6.1g, 수율 83%)을 얻었다. Compound Cpd 131 (6.1 g, yield 83%) was obtained in the same manner as in Example 8, but using compound Inv 11 instead of compound Inv 8.
HRMS [M]+: 738.191HRMS [M] + : 738.191
[[
합성예Synthesis Example
29] 29]
CpdCpd
139의 합성 Synthesis of 139
상기 반응예 9과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 11을 사용하여 화합물 Cpd 139 (4.8g, 수율 87%)을 얻었다. Compound Cpd 139 (4.8 g, yield 87%) was obtained in the same manner as in Example 9, but using compound Inv 11 instead of compound Inv 8.
HRMS [M]+: 559.118HRMS [M] + : 559.118
[[
반응예Example of reaction
30] 30]
CpdCpd
144의 합성 144 Synthesis
상기 반응예 10과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 11을 사용하여 화합물 Cpd 144 (6.0g, 수율 84%)을 얻었다. Compound Cpd 144 (6.0 g, yield 84%) was obtained in the same manner as in Example 10, but using compound Inv 11 instead of compound Inv 8.
HRMS [M]+: 711.180HRMS [M] + : 711.180
[[
합성예Synthesis Example
31] 31]
CpdCpd
148의 합성 Synthesis of 148
상기 반응예 1과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 1을 사용하여 화합물 Cpd 148 (6.2g, 수율 89%)을 얻었다. Compound Cpd 148 (6.2 g, yield 89%) was obtained in the same manner as in Example 1 except that compound Inv 1 was used instead of compound Inv 2.
HRMS [M]+: 630.206HRMS [M] + : 630.206
[[
반응예Example of reaction
32] 32]
CpdCpd
154의 합성 Synthesis of 154
상기 반응예 3과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 1을 사용하여 화합물 Cpd 154 (7.8g, 수율 90%)을 얻었다. Compound Cpd 154 (7.8 g, yield 90%) was obtained in the same manner as in Example 3, using compound Inv 1 instead of compound Inv 2.
HRMS [M]+: 706.237HRMS [M] + : 706.237
[[
반응예Example of reaction
33] 33]
CpdCpd
155의 합성 155 composites
상기 반응예 4과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 1을 사용하여 화합물 Cpd 155 (6.1g, 수율 87%)을 얻었다. Compound Cpd 155 (6.1 g, yield 87%) was obtained in the same manner as in Example 4 except using compound Inv 1 instead of compound Inv 2.
HRMS [M]+: 706.237HRMS [M] + : 706.237
[[
합성예Synthesis Example
34] 34]
CpdCpd
163의 합성 Synthesis of 163
상기 반응예 2과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 1을 사용하여 화합물 Cpd 163 (12.0g, 수율 74%)을 얻었다. Compound Cpd 163 (12.0 g, yield 74%) was obtained in the same manner as in Example 2, using Compound Inv 1 instead of Compound Inv 2.
HRMS [M]+: 527.163HRMS [M] + : 527.163
[[
반응예Example of reaction
35] 35]
CpdCpd
168의 합성 168 Synthesis
*상기 반응예 5과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 1을 사용하여 화합물 Cpd 168 (5.7g, 수율 84%)을 얻었다. * The same procedure as in Reaction Example 5 was performed, except that Compound Inv 1 was used instead of Compound Inv 2 to obtain Compound Cpd 168 (5.7 g, 84% yield).
HRMS [M]+: 679.226HRMS [M] + : 679.226
[[
합성예Synthesis Example
36] 36]
CpdCpd
172의 합성 172 composites
상기 반응예 6과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 7을 사용하여 화합물 Cpd 172 (5.4g, 수율 82%)을 얻었다. Compound Cpd 172 (5.4 g, yield 82%) was obtained in the same manner as in Example 6 except that compound Inv 7 was used instead of compound Inv 8.
HRMS [M]+: 662.160HRMS [M] + : 662.160
[[
반응예Example of reaction
37] 37]
CpdCpd
178의 합성 178 Synthesis
상기 반응예 7과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 7을 사용하여 화합물 Cpd 178 (6.0g, 수율 81%)을 얻었다. Compound Cpd 178 (6.0 g, 81% yield) was obtained in the same manner as in Example 7, except that compound Inv 7 was used instead of compound Inv 8.
HRMS [M]+: 738.191HRMS [M] + : 738.191
[[
반응예Example of reaction
38] 38]
CpdCpd
179의 합성 179 composites
상기 반응예 8과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 7을 사용하여 화합물 Cpd 179 (6.1g, 수율 83%)을 얻었다. Compound Cpd 179 (6.1 g, yield 83%) was obtained in the same manner as in Example 8, but using compound Inv 7 instead of compound Inv 8.
HRMS [M]+: 738.191HRMS [M] + : 738.191
[[
합성예Synthesis Example
39] 39]
CpdCpd
187의 합성 187 Synthesis
상기 반응예 9과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 7을 사용하여 화합물 Cpd 187 (4.8g, 수율 87%)을 얻었다. Compound Cpd 187 (4.8 g, yield 87%) was obtained in the same manner as in Example 9 except that compound Inv 7 was used instead of compound Inv 8.
HRMS [M]+: 559.118HRMS [M] + : 559.118
[[
반응예Example of reaction
40] 40]
CpdCpd
192의 합성 192 Synthesis
상기 반응예 10과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 7을 사용하여 화합물 Cpd 192 (6.0g, 수율 84%)을 얻었다. Compound Cpd 192 (6.0 g, yield 84%) was obtained in the same manner as in Example 10, but using compound Inv 7 instead of compound Inv 8.
HRMS [M]+: 711.180HRMS [M] + : 711.180
[[
합성예Synthesis Example
41] 41]
CpdCpd
196의 합성 196 Synthesis
상기 반응예 1과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 3을 사용하여 화합물 Cpd 196 (6.2g, 수율 89%)을 얻었다. Compound Cpd 196 (6.2 g, yield 89%) was obtained in the same manner as in Example 1 except that compound Inv 3 was used instead of compound Inv 2.
HRMS [M]+: 630.206HRMS [M] + : 630.206
[[
반응예Example of reaction
42] 42]
CpdCpd
202의 합성 202 synthesis
상기 반응예 3과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 3을 사용하여 화합물 Cpd 202 (7.8g, 수율 90%)을 얻었다. Compound Cpd 202 (7.8 g, 90% yield) was obtained in the same manner as in Example 3, using Compound Inv 3 instead of Compound Inv 2.
HRMS [M]+: 706.237HRMS [M] + : 706.237
[[
반응예Example of reaction
43] 43]
CpdCpd
203의 합성 Synthesis of 203
상기 반응예 4과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 3을 사용하여 화합물 Cpd 203 (6.1g, 수율 87%)을 얻었다. Compound Cpd 203 (6.1 g, yield 87%) was obtained in the same manner as in Example 4 except using compound Inv 3 instead of compound Inv 2.
HRMS [M]+: 706.237HRMS [M] + : 706.237
[[
합성예Synthesis Example
44] 44]
CpdCpd
211의 합성 Synthesis of 211
상기 반응예 2과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 3을 사용하여 화합물 Cpd 211 (12.0g, 수율 74%)을 얻었다. A compound Cpd 211 (12.0 g, yield 74%) was obtained by performing the same process as in Example 2, but using compound Inv 3 instead of compound Inv 2.
HRMS [M]+: 527.163HRMS [M] + : 527.163
[[
반응예Example of reaction
45] 45]
CpdCpd
216의 합성 216 composites
상기 반응예 5과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 3을 사용하여 화합물 Cpd 216 (5.7g, 수율 84%)을 얻었다. Compound Cpd 216 (5.7 g, yield 84%) was obtained in the same manner as in Example 5 except that compound Inv 3 was used instead of compound Inv 2.
HRMS [M]+: 679.226HRMS [M] + : 679.226
[[
합성예Synthesis Example
46] 46]
CpdCpd
220의 합성 220 composites
*상기 반응예 6과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 9을 사용하여 화합물 Cpd 220 (5.4g, 수율 82%)을 얻었다. * Compound Cpd 220 (5.4 g, yield 82%) was obtained in the same manner as in Example 6 except that compound Inv 9 was used instead of compound Inv 8.
HRMS [M]+: 662.160HRMS [M] + : 662.160
[[
반응예Example of reaction
47] 47]
CpdCpd
226의 합성 Synthesis of 226
상기 반응예 7과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 9을 사용하여 화합물 Cpd 226 (6.0g, 수율 81%)을 얻었다. Compound Cpd 226 (6.0 g, 81% yield) was obtained in the same manner as in Example 7, except that compound Inv 9 was used instead of compound Inv 8.
HRMS [M]+: 738.191HRMS [M] + : 738.191
[[
반응예Example of reaction
48] 48]
CpdCpd
227의 합성 Synthesis of 227
상기 반응예 8과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 9을 사용하여 화합물 Cpd 227 (6.1g, 수율 83%)을 얻었다. Compound Cpd 227 (6.1 g, yield 83%) was obtained in the same manner as in Example 8 except that compound Inv 9 was used instead of compound Inv 8.
HRMS [M]+: 738.191HRMS [M] + : 738.191
[[
합성예Synthesis Example
49] 49]
CpdCpd
235의 합성 Synthesis of 235
상기 반응예 9과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 9을 사용하여 화합물 Cpd 235 (4.8g, 수율 87%)을 얻었다. Compound Cpd 235 (4.8 g, yield 87%) was obtained in the same manner as in Example 9 except that compound Inv 9 was used instead of compound Inv 8.
HRMS [M]+: 559.118HRMS [M] + : 559.118
[[
반응예Example of reaction
50] 50]
CpdCpd
240의 합성 240 composites
상기 반응예 10과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 9을 사용하여 화합물 Cpd 240 (6.0g, 수율 84%)을 얻었다. Compound Cpd 240 (6.0 g, yield 84%) was obtained in the same manner as in Example 10, but using compound Inv 9 instead of compound Inv 8.
HRMS [M]+: 711.180HRMS [M] + : 711.180
[[
합성예Synthesis Example
51] 51]
CpdCpd
244의 합성 Synthesis of 244
상기 반응예 1과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 6을 사용하여 화합물 Cpd 244 (6.2g, 수율 89%)을 얻었다. Compound Cpd 244 (6.2 g, yield 89%) was obtained in the same manner as in Example 1 except that compound Inv 6 was used instead of compound Inv 2.
HRMS [M]+: 630.206HRMS [M] + : 630.206
[[
반응예Example of reaction
52] 52]
CpdCpd
250의 합성 250 composites
상기 반응예 3과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 6을 사용하여 화합물 Cpd 250 (7.8g, 수율 90%)을 얻었다. Compound Cpd 250 (7.8 g, 90% yield) was obtained by performing the same procedure as in Example 3, but using compound Inv 6 instead of compound Inv 2.
HRMS [M]+: 706.237HRMS [M] + : 706.237
[[
반응예Example of reaction
53] 53]
CpdCpd
251의 합성 Synthesis of 251
상기 반응예 4과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 6을 사용하여 화합물 Cpd 251 (6.1g, 수율 87%)을 얻었다. Compound Cpd 251 (6.1 g, yield 87%) was obtained in the same manner as in Example 4, using Compound Inv 6 instead of Compound Inv 2.
HRMS [M]+: 706.237HRMS [M] + : 706.237
[[
합성예Synthesis Example
54] 54]
CpdCpd
259의 합성 Synthesis of 259
상기 반응예 2과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 6을 사용하여 화합물 Cpd 259 (12.0g, 수율 74%)을 얻었다. Compound Cpd 259 (12.0 g, yield 74%) was obtained in the same manner as in Example 2 except that compound Inv 6 was used instead of compound Inv 2.
HRMS [M]+: 527.163HRMS [M] + : 527.163
[[
반응예Example of reaction
55] 55]
CpdCpd
264의 합성 264 synthesis
상기 반응예 5과 동일한 과정을 수행하되, 화합물 Inv 2 대신 화합물 Inv 6을 사용하여 화합물 Cpd 264 (5.7g, 수율 84%)을 얻었다. Compound Cpd 264 (5.7 g, yield 84%) was obtained in the same manner as in Example 5 except that compound Inv 6 was used instead of compound Inv 2.
HRMS [M]+: 679.226HRMS [M] + : 679.226
[[
합성예Synthesis Example
56] 56]
CpdCpd
268의 합성 Synthesis of 268
상기 반응예 6과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 12을 사용하여 화합물 Cpd 268 (5.4g, 수율 82%)을 얻었다. Compound Cpd 268 (5.4 g, yield 82%) was obtained in the same manner as in Example 6 except that compound Inv 12 was used instead of compound Inv 8.
HRMS [M]+: 662.160HRMS [M] + : 662.160
[[
반응예Example of reaction
57] 57]
CpdCpd
274의 합성 Synthesis of 274
상기 반응예 7과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 12을 사용하여 화합물 Cpd 274 (6.0g, 수율 81%)을 얻었다. Compound Cpd 274 (6.0 g, 81% yield) was obtained in the same manner as in Example 7, except that compound Inv 12 was used instead of compound Inv 8.
HRMS [M]+: 738.191HRMS [M] + : 738.191
[[
반응예Example of reaction
58] 58]
CpdCpd
275의 합성 275 composites
상기 반응예 8과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 12을 사용하여 화합물 Cpd 275 (6.1g, 수율 83%)을 얻었다. Compound Cpd 275 (6.1 g, yield 83%) was obtained in the same manner as in Example 8, but using compound Inv 12 instead of compound Inv 8.
HRMS [M]+: 738.191HRMS [M] + : 738.191
[[
합성예Synthesis Example
59] 59]
CpdCpd
283의 합성 283 Synthesis
상기 반응예 9과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 12을 사용하여 화합물 Cpd 283 (4.8g, 수율 87%)을 얻었다. Compound Cpd 283 (4.8 g, yield 87%) was obtained in the same manner as in Example 9, but using compound Inv 12 instead of compound Inv 8.
HRMS [M]+: 559.118HRMS [M] + : 559.118
[[
반응예Example of reaction
60] 60]
CpdCpd
288의 합성 288 Synthesis
상기 반응예 10과 동일한 과정을 수행하되, 화합물 Inv 8 대신 화합물 Inv 12을 사용하여 화합물 Cpd 288 (6.0g, 수율 84%)을 얻었다. Compound Cpd 288 (6.0 g, yield 84%) was obtained in the same manner as in Example 10, but using compound Inv 12 instead of compound Inv 8.
HRMS [M]+: 711.180HRMS [M] + : 711.180
[[
실시예Example
1 ~ 36] 녹색 유기 1 to 36] green organic
전계Electric field
발광 소자의 제작 Fabrication of light emitting device
반응예 1에서 합성한 화합물 Cpd 4을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 녹색 유기 전계 발광 소자를 제작하였다.Compound Cpd 4 synthesized in Reaction Example 1 was subjected to high purity sublimation purification by a conventionally known method, and then a green organic EL device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ 합성예의 각각의 화합물을 + 10 % Ir(ppy)3 (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다. M-MTDATA (60 nm) / TCTA (80 nm) / each compound of the synthesis example was added to + 10% Ir (ppy) 3 (30nm) / BCP (10 nm) / Alq 3 (30 nm) on the thus prepared ITO transparent electrode. / LiF (1 nm) / Al (200 nm) was laminated in order to manufacture an organic EL device.
m-MTDATA, TCTA, Ir(ppy)3, CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, TCTA, Ir (ppy) 3 , CBP and BCP are as follows.
[비교예 1] 녹색 유기 전계 발광 소자의 제작Comparative Example 1 Fabrication of Green Organic Electroluminescent Device
발광층 형성시 발광 호스트 물질로서 반응예 1에서 합성한 화합물 Cpd 4 대신 CBP를 사용하는 것을 제외하고는 실시예 1과 동일한 과정으로 녹색 유기 전계 발광 소자를 제작하였다.A green organic electroluminescent device was manufactured in the same manner as in Example 1, except that CBP was used instead of the compound Cpd 4 synthesized in Reaction Example 1 as a light emitting host material.
[평가예 1][Evaluation Example 1]
실시예 1 ~ 36 및 비교예 1에서 제작한 각각의 녹색 유기 전계 발광 소자에 대하여 전류밀도 (10) mA/㎠에서의 구동전압, 전류효율 및 발광 피크를 측정하고, 그 결과를 하기 표 1에 나타내었다.For each of the green organic electroluminescent devices fabricated in Examples 1 to 36 and Comparative Example 1, the driving voltage, current efficiency, and emission peak at current density (10) mA / cm 2 were measured, and the results are shown in Table 1 below. Indicated.
| 샘플Sample | 호스트Host | 구동 전압(V)Drive voltage (V) | EL 피크(nm)EL peak (nm) | 전류효율(cd/A)Current efficiency (cd / A) |
| 실시예 1Example 1 | Cpd 4Cpd 4 | 6.82 6.82 | 518 518 | 39.9 39.9 |
| 실시예 2Example 2 | Cpd 10Cpd 10 | 6.98 6.98 | 517 517 | 40.2 40.2 |
| 실시예 3Example 3 | Cpd 11Cpd 11 | 6.89 6.89 | 515 515 | 38.4 38.4 |
| 실시예 4Example 4 | Cpd 28Cpd 28 | 6.78 6.78 | 518 518 | 42.4 42.4 |
| 실시예 5Example 5 | Cpd 34Cpd 34 | 6.69 6.69 | 518 518 | 42.8 42.8 |
| 실시예 6Example 6 | Cpd 35Cpd 35 | 6.72 6.72 | 517 517 | 41.7 41.7 |
| 실시예 7Example 7 | Cpd 52Cpd 52 | 6.70 6.70 | 515 515 | 42.0 42.0 |
| 실시예 8Example 8 | Cpd 58Cpd 58 | 6.82 6.82 | 518 518 | 40.3 40.3 |
| 실시예 9Example 9 | Cpd 59Cpd 59 | 6.84 6.84 | 518 518 | 41.2 41.2 |
| 실시예 10Example 10 | Cpd 76Cpd 76 | 7.20 7.20 | 525 525 | 36.4 36.4 |
| 실시예 11Example 11 | Cpd 82Cpd 82 | 6.82 6.82 | 518 518 | 39.9 39.9 |
| 실시예 12Example 12 | Cpd 83Cpd 83 | 6.98 6.98 | 517 517 | 40.2 40.2 |
| 실시예 13Example 13 | Cpd 100Cpd 100 | 6.89 6.89 | 515 515 | 38.4 38.4 |
| 실시예 14Example 14 | Cpd 106Cpd 106 | 6.78 6.78 | 518 518 | 41.4 41.4 |
| 실시예 15Example 15 | Cpd 107Cpd 107 | 6.69 6.69 | 518 518 | 42.3 42.3 |
| 실시예 16Example 16 | Cpd 124Cpd 124 | 6.72 6.72 | 517 517 | 41.7 41.7 |
| 실시예 17Example 17 | Cpd 130Cpd 130 | 6.70 6.70 | 515 515 | 41.3 41.3 |
| 실시예 18Example 18 | Cpd 131Cpd 131 | 6.82 6.82 | 518 518 | 40.6 40.6 |
| 실시예 19Example 19 | Cpd 148Cpd 148 | 6.84 6.84 | 518 518 | 41.0 41.0 |
| 실시예 20Example 20 | Cpd 154Cpd 154 | 6.78 6.78 | 518 518 | 41.1 41.1 |
| 실시예 21Example 21 | Cpd 155Cpd 155 | 6.69 6.69 | 518 518 | 42.3 42.3 |
| 실시예 22Example 22 | Cpd 172Cpd 172 | 6.72 6.72 | 517 517 | 41.2 41.2 |
| 실시예 23Example 23 | Cpd 178Cpd 178 | 6.70 6.70 | 515 515 | 41.4 41.4 |
| 실시예 24Example 24 | Cpd 179Cpd 179 | 6.82 6.82 | 518 518 | 40.1 40.1 |
| 실시예 25Example 25 | Cpd 196Cpd 196 | 6.84 6.84 | 518 518 | 39.8 39.8 |
| 실시예 26Example 26 | Cpd 202Cpd 202 | 6.786.78 | 515515 | 42.442.4 |
| 실시예 27Example 27 | Cpd 203Cpd 203 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 28Example 28 | Cpd 220Cpd 220 | 6.636.63 | 518518 | 40.540.5 |
| 실시예 29Example 29 | Cpd 226Cpd 226 | 6.786.78 | 515515 | 42.442.4 |
| 실시예 30Example 30 | Cpd 227Cpd 227 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 31Example 31 | Cpd 244Cpd 244 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 32Example 32 | Cpd 250Cpd 250 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 33Example 33 | Cpd 251Cpd 251 | 6.796.79 | 517517 | 40.840.8 |
| 실시예 34Example 34 | Cpd 268Cpd 268 | 6.786.78 | 515515 | 42.442.4 |
| 실시예 35Example 35 | Cpd 274Cpd 274 | 6.816.81 | 518518 | 41.141.1 |
| 실시예 36Example 36 | Cpd 275Cpd 275 | 6.796.79 | 517517 | 40.840.8 |
| 비교예 1Comparative Example 1 | CBPCBP | 6.936.93 | 516516 | 38.238.2 |
상기 표 1에 나타낸 바와 같이, 본 발명에 따른 화합물을 발광층 재료로 각각 사용한 실시예 1 내지 36의 녹색 유기 전계 발광 소자의 경우, 종래 CBP를 사용한 비교예 1의 녹색 유기 전계 발광 소자에 비해 전류 효율 및 구동 전압 면에서 보다 우수한 성능을 나타내는 것을 알 수 있었다.As shown in Table 1, the green organic electroluminescent devices of Examples 1 to 36 each using the compound according to the present invention as a light emitting layer material, compared to the green organic electroluminescent device of Comparative Example 1 using the conventional CBP And better performance in terms of driving voltage.
[실시예 37 ~ 50] 적색 유기 전계 발광 소자의 제조Examples 37 to 50 Fabrication of Red Organic Electroluminescent Device
반응예 2에서 합성한 화합물 Cpd 19을 통상적으로 알려진 방법으로 고순도 승화정제를 한 후 아래의 과정에 따라 적색 유기 전계 발광 소자를 제작하였다.Compound Cpd 19 synthesized in Reaction Example 2 was subjected to high purity sublimation purification by a conventionally known method, and then a red organic EL device was manufactured according to the following procedure.
먼저, ITO (Indium tin oxide)가 1500Å 두께로 박막 코팅된 유리 기판을 증류수 초음파로 세척하였다. 증류수 세척이 끝나면 이소프로필 알코올, 아세톤, 메탄올 등의 용제로 초음파 세척을 하고 건조시킨 후 UV OZONE 세정기 (Power sonic 405, 화신테크)로 이송시킨 다음 UV를 이용하여 상기 기판을 5분간 세정하고 진공 증착기로 기판을 이송하였다.First, a glass substrate coated with ITO (Indium tin oxide) having a thickness of 1500 Å was washed with distilled water ultrasonic waves. After washing the distilled water, ultrasonic cleaning with a solvent such as isopropyl alcohol, acetone, methanol, etc. is dried and transferred to a UV OZONE cleaner (Power sonic 405, Hwasin Tech). The substrate was transferred to.
이렇게 준비된 ITO 투명 전극 위에 m-MTDATA (60 nm)/TCTA (80 nm)/ 합성예의 화합물 + 10 % (piq)2Ir(acac) (30nm)/BCP (10 nm)/Alq3 (30 nm)/LiF (1 nm)/Al (200 nm) 순으로 적층하여 유기 전계 발광 소자를 제작하였다.M-MTDATA (60 nm) / TCTA (80 nm) / Compound of Synthesis Example + 10% (piq) 2 Ir (acac) (30 nm) / BCP (10 nm) / Alq 3 (30 nm) on the thus prepared ITO transparent electrode / LiF (1 nm) / Al (200 nm) was laminated in order to manufacture an organic EL device.
[비교예 2] 적색 유기 전계 발광 소자의 제조Comparative Example 2 Fabrication of Red Organic Electroluminescent Device
발광층 형성시 발광 호스트 물질로서 상기 반응예 2에서 합성한 화합물 Cpd 19 대신 CBP를 사용하는 것을 제외하고는 상기 실시예 37 와 동일한 과정으로 적색 유기 전계 발광 소자를 제작하였다.A red organic electroluminescent device was manufactured in the same manner as in Example 37, except for using CBP instead of the compound Cpd 19 synthesized in Reaction Example 2 as a light emitting host material.
상기 실시예 37 ~ 50 및 비교예 2에서 사용된 m-MTDATA, (piq)2Ir(acac), CBP 및 BCP의 구조는 하기와 같다.The structures of m-MTDATA, (piq) 2 Ir (acac), CBP and BCP used in Examples 37 to 50 and Comparative Example 2 are as follows.
[평가예 2][Evaluation Example 2]
실시예 37 ~ 50 및 비교예 2 에서 제작한 각각의 유기 전계 발광 소자에 대하여 전류밀도 10 mA/㎠에서의 구동전압 및 전류효율을 측정하고, 그 결과를 하기 표 2에 나타내었다.For each organic electroluminescent device fabricated in Examples 37 to 50 and Comparative Example 2, the driving voltage and the current efficiency at the current density of 10 mA / cm 2 were measured, and the results are shown in Table 2 below.
| 샘플Sample | 호스트Host | 구동 전압(V)Drive voltage (V) | 전류효율(cd/A)Current efficiency (cd / A) |
| 실시예 37Example 37 | Cpd 19Cpd 19 | 4.594.59 | 12.812.8 |
| 실시예 38Example 38 | Cpd 24Cpd 24 | 4.654.65 | 12.012.0 |
| 실시예 39Example 39 | Cpd 43Cpd 43 | 4.924.92 | 10.410.4 |
| 실시예 40Example 40 | Cpd 48Cpd 48 | 4.874.87 | 9.49.4 |
| 실시예 41Example 41 | Cpd 67Cpd 67 | 4.904.90 | 9.89.8 |
| 실시예 42Example 42 | Cpd 72Cpd 72 | 4.774.77 | 11.511.5 |
| 실시예 43Example 43 | Cpd 91Cpd 91 | 4.724.72 | 10.210.2 |
| 실시예 44Example 44 | Cpd 96Cpd 96 | 4.804.80 | 11.011.0 |
| 실시예 45Example 45 | Cpd 115Cpd 115 | 4.594.59 | 12.812.8 |
| 실시예 46Example 46 | Cpd 120Cpd 120 | 4.654.65 | 12.012.0 |
| 실시예 47Example 47 | Cpd 139Cpd 139 | 4.924.92 | 10.410.4 |
| 실시예 48Example 48 | Cpd 144Cpd 144 | 4.874.87 | 9.49.4 |
| 실시예 49Example 49 | Cpd 163Cpd 163 | 4.904.90 | 9.89.8 |
| 실시예 50Example 50 | Cpd 168Cpd 168 | 4.824.82 | 11.511.5 |
| 실시예 51Example 51 | Cpd 187Cpd 187 | 4.724.72 | 10.210.2 |
| 실시예 52Example 52 | Cpd 192Cpd 192 | 4.774.77 | 10.810.8 |
| 실시예 53Example 53 | Cpd 211Cpd 211 | 4.804.80 | 10.410.4 |
| 실시예 54Example 54 | Cpd 216Cpd 216 | 4.544.54 | 12.112.1 |
| 실시예 45Example 45 | Cpd 235Cpd 235 | 4.654.65 | 12.012.0 |
| 실시예 46Example 46 | Cpd 240Cpd 240 | 4.924.92 | 10.410.4 |
| 실시예 47Example 47 | Cpd 259Cpd 259 | 4.874.87 | 9.49.4 |
| 실시예 48Example 48 | Cpd 264Cpd 264 | 4.904.90 | 9.89.8 |
| 실시예 49Example 49 | Cpd 283Cpd 283 | 4.774.77 | 11.511.5 |
| 실시예 50Example 50 | Cpd 288Cpd 288 | 4.874.87 | 9.49.4 |
| 비교예 2Comparative Example 2 | CBPCBP | 5.255.25 | 8.28.2 |
상기 표 2에 나타낸 바와 같이, 본 발명에 따른 화합물을 적색 유기 전계 발광 소자의 발광층의 재료로 사용하였을 경우(실시예 37~50) 종래 CBP를 발광층의 재료로 사용한 적색 유기 전계 발광 소자(비교예 2)와 비교해 볼 때 효율 및 구동전압 면에서 우수한 성능을 나타내는 것을 알 수 있다.As shown in Table 2 above, when the compound according to the present invention was used as a material of the light emitting layer of the red organic electroluminescent device (Examples 37 to 50), a red organic electroluminescent device using a conventional CBP as a material of the light emitting layer (comparative example) Compared with 2), it shows excellent performance in terms of efficiency and driving voltage.
이상을 통해 본 발명의 바람직한 실시예에 대하여 설명하였지만, 본 발명은 이에 한정되는 것이 아니고 특허청구범위와 발명의 상세한 설명의 범위 안에서 여러 가지로 변형하여 실시하는 것이 가능하고 이 또한 발명의 범주에 속하는 것은 당연하다.Although the preferred embodiments of the present invention have been described above, the present invention is not limited thereto, and various modifications and changes can be made within the scope of the claims and the detailed description of the invention, which also fall within the scope of the invention. It is natural.
본 발명은 유기 전계 발광 소자용 재료로서 사용될 수 있는 신규 유기 화합물 및 이를 포함하는 유기 전계 발광 소자에 관한 것이다.The present invention relates to novel organic compounds that can be used as materials for organic electroluminescent devices and organic electroluminescent devices comprising the same.
Claims (12)
- 하기 화학식 1로 표시되는 화합물:Compound represented by the following formula (1):[화학식 1][Formula 1]
상기 화학식 1에서,In Chemical Formula 1,R1과 R2, R2와 R3, R3와 R4, R5와 R6, R6과 R7 및 R7과 R8 중 적어도 하나는 하기 화학식 2 내지 4 중 어느 하나로 표시되는 고리와 축합되어 축합 고리를 형성하며;At least one of R 1 and R 2 , R 2 and R 3 , R 3 and R 4 , R 5 and R 6 , R 6 and R 7, and R 7 and R 8 is a ring represented by one of the following Chemical Formulas 2 to 4 Condensed with to form a condensed ring;[화학식 2][Formula 2]
[화학식 3][Formula 3]
[화학식 4][Formula 4]
상기 화학식 1 내지 4에서, In Chemical Formulas 1 to 4,점선은 축합이 이루어지는 부분이며;The dotted line is the part where condensation takes place;X1 내지 X3는 각각 독립적으로 O, S, N(Ar1), C(Ar2)(Ar3) 및 Si(Ar4)(Ar5)로 구성된 군으로부터 선택되나, X1 내지 X3 중 적어도 하나는 N(Ar1)이고;X 1 to X 3 are each independently selected from the group consisting of O, S, N (Ar 1 ), C (Ar 2 ) (Ar 3 ) and Si (Ar 4 ) (Ar 5 ), but X 1 to X 3 At least one of is N (Ar 1 );Y1 내지 Y6은 각각 독립적으로 N 또는 C(R9)이며;Y 1 to Y 6 are each independently N or C (R 9 );Ar1 내지 Ar5는 각각 독립적으로 C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C1~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접한 기와 결합하여 축합 고리를 형성할 수 있고;Ar 1 Ar 5 is each independently C 1 ~ C 40 Alkyl group, C 2 ~ C 40 Alkenyl group, C 2 ~ C 40 Alkynyl group, C 3 ~ C 40 Cycloalkyl group, 3 to 40 heteroatoms Cycloalkyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 aryloxy group, C 1 ~ C 40 alkyl Of silyl group, C 6 ~ C 60 arylsilyl group, C 1 ~ C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 arylphosphanyl group, C 6 ~ C 60 selected from mono or diaryl phosphine group P and the group consisting of C 6 ~ C 60 aryl amine, or by combining adjacent groups may form a condensed ring;상기 화학식 2 내지 4로 표시되는 고리와 축합 고리를 형성하지 않는 R1 내지 R8와, R9는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되고, 상기 R9가 복수 개인 경우 복수 개의 R9는 서로 동일하거나 상이하며; R 1 to R 8 and R 9 which do not form a condensed ring with the ring represented by Formula 2 to 4, and R 9 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, alkyl group of C 1 to C 40 , C 2 to C 40 alkenyl group, C 2 to C 40 alkynyl group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 60 aryl group, nuclear atom 5 To 60 heteroaryl groups, C 1 to C 40 alkyloxy group, C 6 to C 60 aryloxy group, C 3 to C 40 alkylsilyl group, C 6 to C 60 arylsilyl group, C 1 to C 40 alkyl boron group, C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl Phosphinicosuccinic aryl group and a C 6 ~ C 60 amine group is selected from the group consisting of, wherein R 9, when a plurality of individual plurality of R 9 is the same as or different from each other;상기 Ar1 내지 Ar5 및 R1 내지 R9의 알킬기, 알케닐기, 알키닐기, 시클로알킬기, 헤테로시클로알킬기, 아릴기, 헤테로아릴기, 알킬옥시기, 아릴옥시기, 알킬실릴기, 아릴실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴아민기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.Ar 1 Alkyl group, alkenyl group, alkynyl group, cycloalkyl group, heterocycloalkyl group, aryl group, heteroaryl group, alkyloxy group, aryloxy group, alkylsilyl group, arylsilyl group, alkyl boron of Ar 5 to R 1 to R 9 Group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylamine group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenes group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, an aryloxy group of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60, alkyloxy group of C 1 ~ C 40 of the , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group , C 6 ~ C 60 aryl boron group, C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group When substituted or unsubstituted with one or more selected substituents and substituted with a plurality of substituents, they are the same or different from each other. - 제1항에 있어서,The method of claim 1,상기 화합물은 하기 화학식 A-1 내지 A-9 중 어느 하나로 표시되는 화합물:The compound is a compound represented by any one of formulas A-1 to A-9:
상기 화학식 A-1 내지 A-9에서,In Chemical Formulas A-1 to A-9,X1 내지 X3, R1 내지 R6, R8 및 Y1 내지 Y6 각각은 제1항에서 정의된 바와 같다. X 1 to X 3 , R 1 to R 6 , R 8 and Y 1 to Y 6 are each as defined in claim 1. - 제1항에 있어서,The method of claim 1,상기 R1 내지 R9 및 Ar1 내지 Ar5 중 적어도 하나는 하기 화학식 5로 표시되는 치환기이고, 상기 R1 내지 R9 및 Ar1 내지 Ar5는 서로 동일하거나 상이한 화합물:R 1 to R 9 and Ar 1 At least one of Ar to 5 is a substituent represented by the formula (5), wherein R One To R 9 And Ar 1 To Ar 5 is the same or different from each other:[화학식 5][Formula 5]
상기 화학식 5에서,In Chemical Formula 5,*는 결합되는 부분을 의미하고;* Means the part to be combined;L1 및 L2는 각각 독립적으로 단일결합, C6~C18의 아릴렌기 및 핵원자수 5 내지 18개의 헤테로아릴렌기로 이루어진 군에서 선택되며; L 1 and L 2 are each independently selected from the group consisting of a single bond, an arylene group having 6 to 18 carbon atoms and a heteroarylene group having 5 to 18 nuclear atoms;R10은 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성하며; R 10 is hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups , C 3 ~ C 40 Alkylsilyl group, C 6 ~ C 60 Arylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phospha A aryl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylamine group, or combine with an adjacent group to form a condensed ring;상기 L1 및 L2의 아릴렌기 및 헤테로아릴렌기와, 상기 R10의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이하다.Wherein L 1 and the L 2 arylene group and a heteroarylene group, an alkyl group of the R 10, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an aryl The amine group, alkylsilyl group, alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 An alkyl group, a C 2 to C 40 alkenyl group, a C 2 to C 40 alkynyl group, a C 6 to C 60 aryl group, a nuclear atom having 5 to 60 heteroaryl groups, a C 6 to C 60 aryloxy group, C 1 ~ C 40 alkyloxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, 3 to 40 heterocycloalkyl group, C 1 ~ C 40 alkylsilyl group, C 1 ~ C 40 Alkyl boron group, C 6 ~ C 60 Aryl boron group, C 6 ~ C 60 Aryl phosphanyl group, C 6 ~ C 60 Mono or diaryl phosphinyl group and C 6 ~ C 6 When unsubstituted or substituted with one or more substituents selected from the group consisting of 0 arylsilyl groups, they are the same or different from each other. - 제3항에 있어서,The method of claim 3,상기 Ar1 및 R9 중 적어도 하나는 상기 화학식 5로 표시되는 치환기인 화합물. Ar 1 And at least one of the R 9 substituent is a compound represented by the formula (5).
- 제3항에 있어서,The method of claim 3,상기 L1 및 L2는 각각 독립적으로 단일결합이거나 하기 화학식 B-1 내지 B-6 중 어느 하나로 표시되는 링커인 화합물:Wherein L 1 and L 2 are each independently a single bond or a linker represented by any one of the following Formulas B-1 to B-6:
상기 화학식 B-1 내지 B-6에서,In Chemical Formulas B-1 to B-6,*는 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;X4 및 X5은 각각 독립적으로 O, S, N(Ar6) 또는 C(Ar7)(Ar8)이며;X 4 and X 5 are each independently O, S, N (Ar 6 ) or C (Ar 7 ) (Ar 8 );X6는 N 또는 C(Ar9)이며;X 6 is N or C (Ar 9 );p는 0 내지 4의 정수이며;p is an integer from 0 to 4;R11은 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C1~C40의 알킬옥시기, C6~C60의 아릴옥시기, C3~C40의 알킬실릴기, C6~C60의 아릴실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R11이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 11 is deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 3 ~ C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl groups, C 6 to C 60 aryl groups, 5 to 60 heteroaryl groups, C 1 to C 40 alkyloxy groups, C 6 to C 60 aryloxy groups, C An alkylsilyl group of 3 to C 40 , an arylsilyl group of C 6 to C 60 , an alkyl boron group of C 1 to C 40, an aryl boron group of C 6 to C 60 , an arylphosphanyl group of C 6 to C 60 , C 6 ~ C 60 It is selected from the group consisting of mono or diaryl phosphinyl group and C 6 ~ C 60 arylamine group, or may be combined with adjacent groups to form a condensed ring, when there are a plurality of R 11 They are Same or different from each other;Ar6 내지 Ar9는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고;Ar 6 to Ar 9 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, selected from the group consisting arylsilyl a C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 of, or by combining tile adjacent to which they are attached may form a condensed ring;상기 R11 및 Ar6 내지 Ar9의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.Alkyl group of said R 11, and Ar 6 to Ar 9, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boronic Group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenes group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, an aryloxy group of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ C 60, alkyloxy group of C 1 ~ C 40 of the , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 Alkyl boron group , the group consisting of C 6 ~ C 60 aryl group of boron, C 6 ~ C 60 aryl phosphazene group, C 6 ~ C 60 mono or diaryl phosphine blood group and a C 6 ~ C 60 aryl group in the silyl When substituted with at least one selected more substituents or unsubstituted and the ring, is substituted with plural substituents, they may be the same or different from each other. - 제3항에 있어서,The method of claim 3,상기 R10은 수소, C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되는 화합물.R 10 is hydrogen, C 1 ~ C 40 Alkyl group, C 6 ~ C 60 An aryl group, a nuclear atom of 5 to 60 heteroaryl group and C 6 ~ C 60 An arylamine group is selected from the group consisting of.
- 제3항에 있어서,The method of claim 3,상기 R10은 하기 화학식 C-1 내지 C-7 중 어느 하나로 표시되는 치환기인 화합물: R 10 is a compound represented by any one of the following Formulas C-1 to C-7:
상기 화학식 C-1 내지 C-7에서,In Chemical Formulas C-1 to C-7,*는 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;Z1 내지 Z5는 각각 독립적으로 N 또는 C(R16)이며;Z 1 to Z 5 are each independently N or C (R 16);T1 및 T2는 각각 독립적으로 단일결합, C(R17)(R18), N(R19), O 및 S로 이루어진 군에서 선택되나, T1 및 T2 모두가 단일결합은 아니며;T 1 and T 2 are each independently selected from the group consisting of a single bond, C (R 17 ) (R 18 ), N (R 19 ), O and S, but not both T 1 and T 2 are single bonds;q 및 r은 각각 독립적으로 0 내지 4의 정수이며;q and r are each independently integers of 0 to 4;R12 및 R13은 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 또는 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R12 및 R13 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 12 and R 13 are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of C 6 ~ C 60, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 An arylphosphanyl group, a C 6 -C 60 mono or diarylphosphinyl group, and a C 6 -C 60 arylsilyl group, or may be combined with an adjacent group to form a condensed ring, and When there are a plurality of R 12 and R 13 each, they are the same or different from each other;R14 내지 R19는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R16 내지 R19 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 14 to R 19 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, C 6 ~ aryloxy C 60, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a nuclear atoms 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 aryl phosphazene group, selected from the group consisting of C 6 ~ C 60 mono or diaryl the Phosphinicosuccinic group and a C 6 ~ with an aryl silyl group of C 60, or combine tile adjacent to which they are attached may form a fused ring, When each of R 16 to R 19 plural is the same or different from each other;상기 R12 내지 R19의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.Alkyl group of said R 12 to R 19, an alkenyl group, an alkynyl group, an aryl group, a heteroaryl group, an aryloxy group, an alkyloxy group, a cycloalkyl group, a heterocycloalkyl group, an arylamine group, an alkylsilyl group, an alkyl boron group, an aryl Boron, arylphosphanyl, mono or diarylphosphinyl and arylsilyl groups are each independently deuterium, halogen, cyano, nitro, C 1 -C 40 alkyl, C 2 -C 40 alkenyl, C Alkynyl group of 2 to C 40 , aryl group of C 6 to C 60 , heteroaryl group of 5 to 60 nuclear atoms, aryloxy group of C 6 to C 60 , alkyloxy group of C 1 to C 40 , C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 heterocycloalkyl group, C 1 ~ alkyl silyl group of C 40, C 1 ~ C 40 group of an alkyl boron, C 6 Aryl boron group of ~ C 60 , C 6 ~ C 60 aryl phosphanyl group, C 6 ~ C 60 mono or diaryl phosphinyl group and C 6 ~ C 60 arylsilyl group When substituted or unsubstituted with one or more substituents, and substituted with a plurality of substituents, they may be the same or different from each other. - 제7항에 있어서,The method of claim 7, wherein상기 R14 및 R15는 각각 독립적으로 수소, C1~C40의 알킬기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기 및 C6~C60의 아릴아민기로 이루어진 군에서 선택되는 화합물.R 14 and R 15 are each independently hydrogen, a C 1 ~ C 40 alkyl group, C 6 ~ C 60 aryl group, 5 to 60 nuclear aryl group and C 6 ~ C 60 arylamine group Compound selected from the group.
- 제3항에 있어서,The method of claim 3,상기 R10은 하기 화학식 D-1 내지 D-24 중 어느 하나로 표시되는 치환기인 화합물:R 10 is a compound represented by any one of the following Formulas D-1 to D-24:
상기 화학식 D-1 내지 D-24에서,In Chemical Formulas D-1 to D-24,*은 결합이 이루어지는 부분을 의미하고;* Means the part where the bond is made;t는 0 내지 5의 정수이며,t is an integer from 0 to 5,u는 0 내지 4의 정수이며;u is an integer from 0 to 4;v는 0 내지 3의 정수이며;v is an integer from 0 to 3;w는 0 내지 2의 정수이며;w is an integer from 0 to 2;q 및 r은 각각 독립적으로 0 내지 4의 정수이며;q and r are each independently integers of 0 to 4;R16 내지 R19는 각각 독립적으로 수소, 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있으며; R 16 to R 19 are each independently hydrogen, deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 alkyloxy group, C 3 to C 40 cycloalkyl group, nuclear atom 3 To 40 heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to mono or diaryl phosphine of C 60 aryl phosphazene group, C 6 ~ C 60 of the blood group and a C 6 ~ C 60 selected from an aryl silyl group the group consisting of or of, by combining groups adjacent to form a condensed ring;R12, R13 및 R20은 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C6~C60의 아릴아민기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택되거나, 인접하는 기와 결합하여 축합 고리를 형성할 수 있고, 상기 R12, R13 및 R20 각각이 복수 개인 경우 이들은 서로 동일하거나 상이하며;R 12 , R 13 and R 20 are deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 ~ C 40 alkynyl group, C 6 ~ C 60 the aryl group, the number of nuclear atoms of 5 to 60 heteroaryl group, an aryloxy group of C 6 ~ C 60, C 1 ~ C 40 alkyloxy group of, C 3 ~ C 40 cycloalkyl group, a number of nuclear atoms of 3 to 40 Heterocycloalkyl groups, C 6 to C 60 arylamine groups, C 1 to C 40 alkylsilyl groups, C 1 to C 40 alkylboron groups, C 6 to C 60 aryl boron groups, C 6 to C 60 An arylphosphanyl group, a C 6 ~ C 60 mono or diaryl phosphinyl group and a C 6 ~ C 60 arylsilyl group, or may be combined with an adjacent group to form a condensed ring, wherein R When there are a plurality of each of 12 , R 13 and R 20 , they are the same as or different from each other;상기 R12, R13 및 R16 내지 R20의 알킬기, 알케닐기, 알키닐기, 아릴기, 헤테로아릴기, 아릴옥시기, 알킬옥시기, 시클로알킬기, 헤테로시클로알킬기, 아릴아민기, 알킬실릴기, 알킬보론기, 아릴보론기, 아릴포스파닐기, 모노 또는 디아릴포스피닐기 및 아릴실릴기는 각각 독립적으로 중수소, 할로겐, 시아노기, 니트로기, C1~C40의 알킬기, C2~C40의 알케닐기, C2~C40의 알키닐기, C6~C60의 아릴기, 핵원자수 5 내지 60개의 헤테로아릴기, C6~C60의 아릴옥시기, C1~C40의 알킬옥시기, C6~C60의 아릴아민기, C3~C40의 시클로알킬기, 핵원자수 3 내지 40개의 헤테로시클로알킬기, C1~C40의 알킬실릴기, C1~C40의 알킬보론기, C6~C60의 아릴보론기, C6~C60의 아릴포스파닐기, C6~C60의 모노 또는 디아릴포스피닐기 및 C6~C60의 아릴실릴기로 이루어진 군에서 선택된 1종 이상의 치환기로 치환되거나 비치환되고, 복수 개의 치환기로 치환되는 경우, 이들은 서로 동일하거나 상이할 수 있다.The alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, aryloxy group, alkyloxy group, cycloalkyl group, heterocycloalkyl group, arylamine group, alkylsilyl group of R 12 , R 13 and R 16 to R 20 , Alkyl boron group, aryl boron group, arylphosphanyl group, mono or diaryl phosphinyl group and arylsilyl group are each independently deuterium, halogen, cyano group, nitro group, C 1 ~ C 40 alkyl group, C 2 ~ C 40 alkenyl group, C 2 to C 40 alkynyl group, C 6 to C 60 aryl group, 5 to 60 heteroaryl groups, C 6 to C 60 aryloxy group, C 1 to C 40 Alkoxyoxy group, C 6 ~ C 60 arylamine group, C 3 ~ C 40 cycloalkyl group, C 3 ~ C 40 heterocycloalkyl group, C 1 ~ C 40 Alkylsilyl group, C 1 ~ C 40 An alkylboron group, a C 6 to C 60 aryl boron group, a C 6 to C 60 arylphosphanyl group, a C 6 to C 60 mono or diarylphosphinyl group, and a C 6 to C 60 arylsilyl group When substituted or unsubstituted with one or more substituents selected from the group, and substituted with a plurality of substituents, they may be the same or different from each other. - 제1항에 있어서,The method of claim 1,상기 화합물은 아래의 화합물로 이루어진 군에서 선택되는 것을 특징으로 하는 화합물: The compound is selected from the group consisting of the following compounds:
- (i) 양극, (ii) 음극, 및 (iii) 상기 양극과 음극 사이에 개재(介在)된 1층 이상의 유기물층을 포함하는 유기 전계 발광 소자로서, An organic electroluminescent device comprising (i) an anode, (ii) a cathode, and (iii) at least one organic material layer interposed between the anode and the cathode,상기 1층 이상의 유기물층 중에서 적어도 하나는 제1항의 화학식 1로 표시되는 화합물을 포함하는 것을 특징으로 하는 유기 전계 발광 소자.At least one of the one or more organic material layer is an organic electroluminescent device, characterized in that it comprises a compound represented by the formula (1) of claim 1.
- 제11항에 있어서,The method of claim 11,상기 화합물을 포함하는 유기물층은 정공 주입층, 정공 수송층, 전자 수송층, 전자 수송 보조층, 전자 주입층, 수명 개선층, 발광층 및 발광 보조층으로 이루어진 군에서 선택되는 유기 전계 발광 소자.The organic material layer including the compound is selected from the group consisting of a hole injection layer, a hole transport layer, an electron transport layer, an electron transport auxiliary layer, an electron injection layer, a life improvement layer, a light emitting layer and a light emitting auxiliary layer.
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| KR20140000640A (en) * | 2012-06-22 | 2014-01-03 | 에스에프씨 주식회사 | Aromatic compound and organoelectroluminescent device comprising the compound |
| KR20140142021A (en) * | 2013-06-03 | 2014-12-11 | 덕산하이메탈(주) | An organic electronic element comprising a layer for improving light efficiency, and an electronic device comprising the same |
| KR20160060572A (en) * | 2014-11-19 | 2016-05-30 | 주식회사 엠비케이 | Organic electroluminescent compound, ink composition, organic electroluminescent device and electric apparatus |
| KR20160078102A (en) * | 2014-12-24 | 2016-07-04 | 주식회사 두산 | Organic compound and organic electroluminescent device comprising the same |
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| KR20140000640A (en) * | 2012-06-22 | 2014-01-03 | 에스에프씨 주식회사 | Aromatic compound and organoelectroluminescent device comprising the compound |
| KR20140142021A (en) * | 2013-06-03 | 2014-12-11 | 덕산하이메탈(주) | An organic electronic element comprising a layer for improving light efficiency, and an electronic device comprising the same |
| KR20160060572A (en) * | 2014-11-19 | 2016-05-30 | 주식회사 엠비케이 | Organic electroluminescent compound, ink composition, organic electroluminescent device and electric apparatus |
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