WO2013191404A1 - Composé, élément électronique organique l'utilisant, et dispositif électronique à base de celui-ci - Google Patents
Composé, élément électronique organique l'utilisant, et dispositif électronique à base de celui-ci Download PDFInfo
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- WO2013191404A1 WO2013191404A1 PCT/KR2013/005098 KR2013005098W WO2013191404A1 WO 2013191404 A1 WO2013191404 A1 WO 2013191404A1 KR 2013005098 W KR2013005098 W KR 2013005098W WO 2013191404 A1 WO2013191404 A1 WO 2013191404A1
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- Prior art keywords
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- substituted
- aryl
- unsubstituted
- deuterium
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 66
- 125000001424 substituent group Chemical group 0.000 claims description 30
- 238000000034 method Methods 0.000 claims description 24
- 238000002347 injection Methods 0.000 claims description 23
- 239000007924 injection Substances 0.000 claims description 23
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical compound [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 20
- 125000000623 heterocyclic group Chemical group 0.000 claims description 19
- YZCKVEUIGOORGS-NJFSPNSNSA-N Tritium Chemical compound [3H] YZCKVEUIGOORGS-NJFSPNSNSA-N 0.000 claims description 18
- 229910052805 deuterium Inorganic materials 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 239000001257 hydrogen Substances 0.000 claims description 18
- 229910052722 tritium Inorganic materials 0.000 claims description 18
- 125000002560 nitrile group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 16
- 230000005525 hole transport Effects 0.000 claims description 16
- 150000002431 hydrogen Chemical class 0.000 claims description 16
- 239000011368 organic material Substances 0.000 claims description 15
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical group [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 11
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 claims description 10
- 229910052736 halogen Inorganic materials 0.000 claims description 10
- 150000002367 halogens Chemical class 0.000 claims description 10
- 125000005842 heteroatom Chemical group 0.000 claims description 10
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 8
- 125000003277 amino group Chemical group 0.000 claims description 7
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical group [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 6
- 239000000243 solution Substances 0.000 claims description 6
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 229910052698 phosphorus Inorganic materials 0.000 claims description 5
- 229910052717 sulfur Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 229920006395 saturated elastomer Polymers 0.000 claims description 4
- 125000005018 aryl alkenyl group Chemical group 0.000 claims description 3
- 230000008569 process Effects 0.000 claims description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003368 amide group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 238000005286 illumination Methods 0.000 claims description 2
- 150000002825 nitriles Chemical class 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 79
- 230000015572 biosynthetic process Effects 0.000 description 42
- 238000003786 synthesis reaction Methods 0.000 description 41
- 230000000052 comparative effect Effects 0.000 description 32
- 239000012044 organic layer Substances 0.000 description 29
- 239000000463 material Substances 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 27
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 26
- 239000000741 silica gel Substances 0.000 description 26
- 229910002027 silica gel Inorganic materials 0.000 description 26
- 229960001866 silicon dioxide Drugs 0.000 description 26
- 238000001953 recrystallisation Methods 0.000 description 22
- 238000010992 reflux Methods 0.000 description 21
- 239000000203 mixture Substances 0.000 description 17
- 0 *c(c1c2cccc1)cc1c2[n](*)c(cc2)c1cc2Br Chemical compound *c(c1c2cccc1)cc1c2[n](*)c(cc2)c1cc2Br 0.000 description 14
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000002156 mixing Methods 0.000 description 11
- 125000003118 aryl group Chemical group 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 9
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 7
- -1 aryl halide compound Chemical class 0.000 description 7
- 125000004432 carbon atom Chemical group C* 0.000 description 7
- 229940117389 dichlorobenzene Drugs 0.000 description 7
- 101150003085 Pdcl gene Proteins 0.000 description 6
- 238000000151 deposition Methods 0.000 description 6
- KZPYGQFFRCFCPP-UHFFFAOYSA-N 1,1'-bis(diphenylphosphino)ferrocene Chemical compound [Fe+2].C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=C[C-]1P(C=1C=CC=CC=1)C1=CC=CC=C1 KZPYGQFFRCFCPP-UHFFFAOYSA-N 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 5
- 239000000376 reactant Substances 0.000 description 5
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical compound C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- IPWKHHSGDUIRAH-UHFFFAOYSA-N bis(pinacolato)diboron Chemical compound O1C(C)(C)C(C)(C)OB1B1OC(C)(C)C(C)(C)O1 IPWKHHSGDUIRAH-UHFFFAOYSA-N 0.000 description 4
- 229940126214 compound 3 Drugs 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- UEEXRMUCXBPYOV-UHFFFAOYSA-N iridium;2-phenylpyridine Chemical compound [Ir].C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1.C1=CC=CC=C1C1=CC=CC=N1 UEEXRMUCXBPYOV-UHFFFAOYSA-N 0.000 description 4
- 150000002828 nitro derivatives Chemical class 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 125000000732 arylene group Chemical group 0.000 description 3
- 229910052796 boron Inorganic materials 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 238000000434 field desorption mass spectrometry Methods 0.000 description 3
- 230000037361 pathway Effects 0.000 description 3
- AYEKOFBPNLCAJY-UHFFFAOYSA-O thiamine pyrophosphate Chemical compound CC1=C(CCOP(O)(=O)OP(O)(O)=O)SC=[N+]1CC1=CN=C(C)N=C1N AYEKOFBPNLCAJY-UHFFFAOYSA-O 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- 238000006443 Buchwald-Hartwig cross coupling reaction Methods 0.000 description 2
- 229910001508 alkali metal halide Inorganic materials 0.000 description 2
- 150000008045 alkali metal halides Chemical class 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 2
- 238000005885 boration reaction Methods 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 238000001308 synthesis method Methods 0.000 description 2
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 2
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- ZTXCGNFXDGWJJZ-UHFFFAOYSA-N Bc1ccc(C(c2c-3c4ccccc4c4c2cccc4)c2c(-c4ccccc4)nc(-c4ccccc4)nc2)c-3c1 Chemical compound Bc1ccc(C(c2c-3c4ccccc4c4c2cccc4)c2c(-c4ccccc4)nc(-c4ccccc4)nc2)c-3c1 ZTXCGNFXDGWJJZ-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 238000006069 Suzuki reaction reaction Methods 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004891 communication Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 230000001934 delay Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000003618 dip coating Methods 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 125000004404 heteroalkyl group Chemical group 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
- 125000005549 heteroarylene group Chemical group 0.000 description 1
- 125000000592 heterocycloalkyl group Chemical group 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000010295 mobile communication Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- GJVFBWCTGUSGDD-UHFFFAOYSA-L pentamethonium bromide Chemical compound [Br-].[Br-].C[N+](C)(C)CCCCC[N+](C)(C)C GJVFBWCTGUSGDD-UHFFFAOYSA-L 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 238000005240 physical vapour deposition Methods 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 239000011241 protective layer Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000010345 tape casting Methods 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 238000001771 vacuum deposition Methods 0.000 description 1
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- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D209/56—Ring systems containing three or more rings
- C07D209/80—[b, c]- or [b, d]-condensed
- C07D209/82—Carbazoles; Hydrogenated carbazoles
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- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E10/00—Energy generation through renewable energy sources
- Y02E10/50—Photovoltaic [PV] energy
- Y02E10/549—Organic PV cells
Definitions
- the present invention relates to a compound, an organic electric element comprising the same, and an electronic device thereof.
- organic light emitting phenomenon refers to a phenomenon in which electrical energy is converted into light energy using an organic material.
- An organic electric element using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
- the organic layer is often made of a multi-layer structure composed of different materials in order to increase the efficiency and stability of the organic electrical device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer.
- Materials used as the organic material layer in the organic electric element may be classified into light emitting materials and charge transport materials such as hole injection materials, hole transport materials, electron transport materials, electron injection materials and the like depending on their functions.
- the deposition method is the mainstream in the formation of the OLED device, a situation that requires a material that can withstand a long time, that is, a material having a strong heat resistance characteristics.
- a material constituting the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., is supported by a stable and efficient material.
- a stable and efficient organic material layer for an organic electric device has not been made sufficiently, and therefore, the development of new materials is still required.
- An object of the present invention is to provide a compound capable of improving high luminous efficiency, low driving voltage, high heat resistance, color purity, and lifetime of an element, an organic electric element using the same, and an electronic device thereof.
- the present invention provides a compound represented by the following formula (1).
- the present invention provides an organic electronic device using the compound represented by Formula 1 and an electronic device thereof.
- FIG. 1 is an exemplary view of an organic electroluminescent device according to the present invention.
- halo or halogen as used herein includes fluorine, chlorine, bromine and iodine unless otherwise stated.
- alkyl or “alkyl group” has a carbon number of 1 to 60 unless otherwise specified, but is not limited thereto.
- alkenyl or “alkynyl” has a double bond or a triple bond having 2 to 60 carbon atoms, respectively, unless otherwise specified, but is not limited thereto.
- cycloalkyl refers to alkyl forming a ring having 3 to 60 carbon atoms, without being limited thereto.
- alkoxy group used in the present invention has a carbon number of 1 to 60 unless otherwise stated, it is not limited thereto.
- aryl group and “arylene group” have a carbon number of 6 to 60 unless otherwise stated, but is not limited thereto.
- an aryl group or an arylene group means a monocyclic or polycyclic aromatic, and includes an aromatic ring formed by neighboring substituents participating in a bond or a reaction.
- the aryl group may be a phenyl group, a biphenyl group, a fluorene group, a spirofluorene group.
- heteroalkyl means an alkyl including one or more heteroatoms unless otherwise indicated.
- heteroaryl group or “heteroarylene group” means an aryl group or arylene group having 3 to 60 carbon atoms, each of which includes one or more heteroatoms, unless otherwise specified. In addition, it includes not only single ring but also multiple rings, and adjacent groups may be formed by combining.
- heterocycloalkyl includes one or more heteroatoms, unless otherwise indicated, having from 2 to 60 carbon atoms, including single rings as well as multicycles. Adjacent groups may be formed in combination.
- heterocyclic group may mean an alicyclic and / or aromatic including a heteroatom.
- heteroatom refers to N, O, S, P, and Si unless otherwise indicated.
- aliphatic as used herein means an aliphatic hydrocarbon having 1 to 60 carbon atoms
- aliphatic ring means an aliphatic hydrocarbon ring having 3 to 60 carbon atoms.
- saturated or unsaturated ring as used herein means a saturated or unsaturated aliphatic ring or an aromatic ring or heterocyclic ring having 6 to 60 carbon atoms.
- heterocompounds or heteroradicals other than the aforementioned heterocompounds include, but are not limited to, one or more heteroatoms.
- substituted in the term “substituted or unsubstituted” as used in the present invention is deuterium, halogen, amino group, nitrile group, nitro group, C 1 ⁇ C 20 alkyl group, C 1 ⁇ C 20 alkoxy groups, C 1 to C 20 alkylamine groups, C 1 to C 20 alkylthiophene groups, C 6 to C 20 arylthiophene groups, C 2 to C 20 alkenyl groups, C 2 to C 20 alkynyl group, C 3 ⁇ C 20 cycloalkyl group, C 6 ⁇ C 60 aryl group, C 6 ⁇ C 20 aryl group substituted with deuterium, C 8 ⁇ C 20 aryl alkenyl group, silane group, boron Group, germanium group, and C 5 ⁇ C 20 It is meant to be substituted with one or more substituents selected from the group consisting of, but not limited to these substituents.
- FIG. 1 is an exemplary view of an organic electric device according to an embodiment of the present invention.
- the organic electric device 100 includes a first electrode 120, a second electrode 180, a first electrode 110, and a second electrode 180 formed on a substrate 110.
- An organic material layer containing a compound represented by the formula (1) between) is provided.
- the first electrode 120 may be an anode (anode)
- the second electrode 180 may be a cathode (cathode)
- the first electrode may be a cathode and the second electrode may be an anode.
- the organic layer may include a hole injection layer 130, a hole transport layer 140, a light emitting layer 150, an electron transport layer 160, and an electron injection layer 170 on the first electrode 120 in sequence. At this time, the remaining layers except for the light emitting layer 150 may not be formed.
- the hole blocking layer, the electron blocking layer, the light emitting auxiliary layer 151, the buffer layer 141 may be further included, and the electron transport layer 160 may serve as the hole blocking layer.
- the organic electronic device according to the present invention may further include a protective layer formed on one surface of the first electrode and the second electrode opposite to the organic material layer.
- the compound according to the present invention applied to the organic material layer is a hole injection layer 130, a hole transport layer 140, an electron transport layer 160, the electron injection layer 170, the host of the light emitting layer 150 or the material of the dopant or capping layer Can be used as
- the organic electroluminescent device may be manufactured using a PVD method.
- the anode 120 is formed by depositing a metal or a conductive metal oxide or an alloy thereof on a substrate, and the hole injection layer 130, the hole transport layer 140, the light emitting layer 150, and the electron transport layer are formed thereon.
- the organic material layer including the 160 and the electron injection layer 170 it can be prepared by depositing a material that can be used as the cathode 180 thereon.
- the organic material layer using a variety of polymer materials is less by a solution process or solvent process, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer method, rather than deposition
- a solution process or solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing or thermal transfer method, rather than deposition
- the organic material layer according to the present invention can be formed by various methods, and the scope of the present invention is not limited by the method of forming the same.
- the organic electric element according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
- the organic electroluminescent device according to the present invention may be one of an organic electroluminescent device (OLED), an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white illumination device.
- OLED organic electroluminescent device
- OPC organic photoconductor
- organic TFT organic transistor
- Another embodiment of the present invention may include a display device including the organic electric element of the present invention described above, and an electronic device including a control unit for controlling the display device.
- the electronic device may be a current or future wired or wireless communication terminal, and includes all electronic devices such as a mobile communication terminal such as a mobile phone, a PDA, an electronic dictionary, a PMP, a remote controller, a navigation device, a game machine, various TVs, and various computers.
- the compound according to one aspect of the present invention is represented by the following formula (1).
- Ar One And Ar 2 are each independently hydrogen, deuterium, tritium, halogen, amino, nitrile, nitro, C One ⁇ C 20 Alkyl group, C One ⁇ C 20 Alkoxy group, C One ⁇ C 20 Alkylamine groups, C 6 ⁇ C 60 Arylamine group, C One ⁇ C 20 Alkylthiophene groups, C 6 ⁇ C 20 Arylthiophene group, C 2 ⁇ C 20 Alkenyl, C 2 ⁇ C 20 Alkynyl, C 3 ⁇ C 20 Cycloalkyl group, C 6 ⁇ C 60 Aryl group of C, substituted with deuterium 6 ⁇ C 60 Aryl group, C 8 ⁇ C 20 Aryl alkenyl group, silane group, boron group, germanium group and C 2 ⁇ C 60 C unsubstituted or substituted with a substituent selected from the group consisting of heterocyclic groups 6 ⁇ C 60 Aryl group; Hydrogen, deuterium, tritium, halogen, C One
- R One To R 12 Each independently of one another is hydrogen; heavy hydrogen; Tritium; Hydrogen, deuterium, tritium, halogen, C One ⁇ C 60 Alkyl group, C One ⁇ C 60 Alkoxy group, C One ⁇ C 60 Alkylamine groups, C 5 ⁇ C 60 Arylamine group, C One ⁇ C 60 Alkylthiophene groups, C 6 ⁇ C 60 Aryl thiophene group, C 2 ⁇ C 60 Alkenyl, C 2 ⁇ C 60 Alkynyl, C 3 ⁇ C 60 Cycloalkyl group, C 6 ⁇ C 60 Aryl group of C, substituted with deuterium 6 ⁇ C 60 Aryl group, C 8 ⁇ C 60 Aryl alkenyl group, substituted or unsubstituted silane group, substituted or unsubstituted boron group, substituted or unsubstituted germanium group and substituted or unsubstituted C 2 ⁇ C 60 Unsubstituted or substituted with a
- R 6 and R 7 , R 9 and R 10 , R 10 and R 11 , R 11 and R 12 may each combine with neighboring groups to form a saturated or unsaturated ring.
- the compound represented by Chemical Formula 1 may be one of the following Chemical Formulas (2) to (6).
- the compound represented by Formula 1 may be one of the following compounds P1-1 to P6-46.
- Sub C can be prepared by the following scheme.
- Sub C compounds synthesized using the synthesis examples are as follows, but are not limited thereto, and their FD-MS are shown in Table 1 below.
- Compound S 1 can be synthesized by the reaction route of Scheme 6 below.
- Compound S 2 can be synthesized by the reaction route of Scheme 7 below.
- Compound S 3 may be synthesized by the reaction pathway of Scheme 8 below.
- Compound S 4 may be synthesized by the reaction pathway of Scheme 9 below.
- Compound S 5 may be synthesized by the reaction pathway of Scheme 10 below.
- the compounds synthesized using the synthesis method of S 1 to S 5 are as follows, which is illustrative but not limited thereto.
- B (pin) is to be.
- the S-2-1 generation step in Scheme 7 and the S-3-1 generation step in Scheme 8 are based on the Suzuki cross-coupilng reaction, the C-1 generation step in Scheme 2, and the C-2 generation step in Scheme 3 , C3 generation step in Scheme 4, C4 generation step in Scheme 5, S-1-2 generation step in Scheme 6, S-2-3 generation step in Scheme 7, S-3-3 generation step in Scheme 8, Scheme 9
- S-4-3 generation step, S-5-2 generation step in Scheme 10, etc. are all based on the Buchwald-Hartwig cross coupling reaction
- the S 3 generation step, the S 4 generation step in Scheme 9, and the S 5 generation step in Scheme 10 are all based on the Miyaura boration reaction. Therefore, it will be appreciated by those skilled in the art that the reaction will proceed with the same mechanism with respect to the compound to which other substituents are attached in addition to the substituents exemplified.
- the hole transport layer by vacuum depositing 2-TNATA on the ITO layer (anode) formed on the organic substrate to form a hole injection layer with a thickness of 60nm, the hole transport layer by vacuum depositing the compound according to the present invention to a thickness of 20nm on the hole injection layer Formed.
- CBP 4,4'-N, N'-dicarbazole-biphenyl
- Ir (ppy) 3 tris (2-phenylpyridine) -iridium] as the dopant material were 9:
- the light emitting layer was deposited by doping to a thickness of 30nm with a weight ratio of 1.
- An organic light emitting display device was manufactured in the same manner as in [Example 8], except that Comparative Compound 1 was used instead of the compound of the present invention when forming the hole transport layer.
- An organic light emitting display device was manufactured in the same manner as in [Example 8], except that Comparative Compound 2 was used instead of the compound of the present invention when forming the hole transport layer.
- An organic light emitting display device was manufactured in the same manner as in [Example 8], except that Comparative Compound 3 was used instead of the compound of the present invention when forming the hole transport layer.
- Example 8 (Example (1) to Example 272) and [Comparative Example 1] to [Comparative Example 3] (Comparative Example (1) to Comparative Example (3) of the present invention prepared as described above
- the electroluminescent (EL) characteristics were measured with a PR-650 photoresearch company by applying a forward bias DC voltage to the organic electroluminescent device of The instrument was measured for T90 life.
- EL electroluminescent
- Example 8 Examples (1) to (272)
- Example 1 to [Comparative Example 3] (Comparative Example (1) to Comparative Example (3)) of the present invention.
- the driving voltage, current density, luminance, luminous efficiency, and lifetime of the organic light emitting diodes were measured, as shown in Table 4 below.
- a copper phthalocyanine (hereinafter abbreviated as CuPc) is vacuum deposited on an ITO layer (anode) formed on a glass substrate to form a hole injection layer having a thickness of 40 nm, and then the compound P3 of the present invention on the hole injection layer.
- -27 was vacuum deposited to a thickness of 20 nm to form a hole transport layer.
- the compound of the present invention was vacuum deposited to a thickness of 20 nm on the hole transport layer to form a light emitting auxiliary layer.
- CBP 4,4'-N, N'-dicarbazole-biphenyl
- Ir (ppy) 3 tris (2-phenylpyridine) iridium
- the light emitting layer was doped to a thickness of 30 nm with a weight ratio of 95: 5.
- the reason why the compound P3-27 of the present invention is used as the hole transport layer material is because, as shown in Table 4, the driving voltage of the organic electric element to which the compound P3-27 is applied is low, the luminous efficiency is high, and the lifetime is also high. to be.
- An organic light emitting display device was manufactured in the same manner as in [Example 9], except that the light emitting auxiliary layer was omitted. That is, an organic light emitting display device was manufactured in the same manner as in [Example 9], except that the light emitting auxiliary layer was not formed.
- An organic light emitting display device was manufactured in the same manner as in [Example 9], except that the Comparative Compound 3 was used to form the emission auxiliary layer instead of the compound of the present invention.
- Example 9 (Examples 273 to 544), [Comparative Example 4] (Comparative Example (4)), and [Comparative Example 5] (Comparative Example (5) of the present invention prepared as described above.
- the electroluminescence (EL) characteristics of the organic electroluminescent elements of)) were applied to the PR-650 photoresearch company by applying a forward bias DC voltage.
- the T95 life was measured with a life measuring instrument.
- the driving voltage, current density, luminance, light emission efficiency, and lifetime of the organic light emitting diodes were measured as shown in Table 5 below.
- the compound according to the present invention is not only an organic electroluminescent device (OLED), but also a display device, an organic solar cell, an organic photoconductor (OPC), an organic transistor (organic TFT), a monochromatic or white lighting element, etc. May also be used.
- the compounds of the present invention are used in other organic material layers of the organic light emitting device, for example, a hole injection layer, a light emitting layer, an electron injection layer, an electron transport layer, the same effect can be obtained.
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Abstract
La présente invention concerne un nouveau composé, un élément organique l'utilisant, et un dispositif électronique à base de celui-ci. Selon la présente invention, le rendement d'émission de lumière, la pureté de couleur et la durée de vie d'un élément peuvent être améliorés, et une tension de commande peut être réduite.
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