WO2012134191A2 - 나프탈렌 유도체, 이를 이용한 유기 재료, 및 이를 이용한 유기 전기발광 소자 - Google Patents
나프탈렌 유도체, 이를 이용한 유기 재료, 및 이를 이용한 유기 전기발광 소자 Download PDFInfo
- Publication number
- WO2012134191A2 WO2012134191A2 PCT/KR2012/002322 KR2012002322W WO2012134191A2 WO 2012134191 A2 WO2012134191 A2 WO 2012134191A2 KR 2012002322 W KR2012002322 W KR 2012002322W WO 2012134191 A2 WO2012134191 A2 WO 2012134191A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- naphthyl
- phenyl
- substituted
- unsubstituted
- hydrogen
- Prior art date
Links
- 150000002790 naphthalenes Chemical class 0.000 title description 8
- 239000011368 organic material Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 93
- 239000000463 material Substances 0.000 claims abstract description 60
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 98
- 239000010410 layer Substances 0.000 claims description 96
- 125000001624 naphthyl group Chemical group 0.000 claims description 88
- -1 6-phenyl-2-naphthyl Chemical group 0.000 claims description 46
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 44
- 239000001257 hydrogen Substances 0.000 claims description 38
- 229910052739 hydrogen Inorganic materials 0.000 claims description 38
- 150000002431 hydrogen Chemical class 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 27
- 238000000034 method Methods 0.000 claims description 26
- 239000004305 biphenyl Chemical group 0.000 claims description 25
- 235000010290 biphenyl Nutrition 0.000 claims description 22
- 239000010409 thin film Substances 0.000 claims description 14
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 claims description 12
- 125000004653 anthracenylene group Chemical group 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004957 naphthylene group Chemical group 0.000 claims description 8
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 8
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 6
- 125000005561 phenanthryl group Chemical group 0.000 claims description 6
- 125000005548 pyrenylene group Chemical group 0.000 claims description 4
- 125000001725 pyrenyl group Chemical group 0.000 claims description 3
- 239000002356 single layer Substances 0.000 claims description 3
- 125000004958 1,4-naphthylene group Chemical group 0.000 claims description 2
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 2
- 125000004959 2,6-naphthylene group Chemical group [H]C1=C([H])C2=C([H])C([*:1])=C([H])C([H])=C2C([H])=C1[*:2] 0.000 claims description 2
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 47
- 238000004020 luminiscence type Methods 0.000 abstract description 9
- 239000000543 intermediate Substances 0.000 description 79
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 64
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 51
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 46
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 46
- 238000002360 preparation method Methods 0.000 description 40
- 238000006243 chemical reaction Methods 0.000 description 33
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 32
- 239000010408 film Substances 0.000 description 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 27
- 239000012044 organic layer Substances 0.000 description 27
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- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 24
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 24
- 238000002347 injection Methods 0.000 description 24
- 239000007924 injection Substances 0.000 description 24
- 229910000027 potassium carbonate Inorganic materials 0.000 description 23
- 238000005481 NMR spectroscopy Methods 0.000 description 21
- 229910052757 nitrogen Inorganic materials 0.000 description 20
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 14
- 239000002019 doping agent Substances 0.000 description 13
- AJSTXXYNEIHPMD-UHFFFAOYSA-N triethyl borate Chemical compound CCOB(OCC)OCC AJSTXXYNEIHPMD-UHFFFAOYSA-N 0.000 description 12
- 230000005525 hole transport Effects 0.000 description 11
- 238000005160 1H NMR spectroscopy Methods 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000011347 resin Substances 0.000 description 9
- 230000032258 transport Effects 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 8
- 239000012300 argon atmosphere Substances 0.000 description 8
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- 239000003054 catalyst Substances 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
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- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 5
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 5
- 229910052751 metal Inorganic materials 0.000 description 5
- 239000002184 metal Substances 0.000 description 5
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical class N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 5
- 125000001424 substituent group Chemical group 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- SPDPTFAJSFKAMT-UHFFFAOYSA-N 1-n-[4-[4-(n-[4-(3-methyl-n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-4-n,4-n-bis(3-methylphenyl)-1-n-phenylbenzene-1,4-diamine Chemical group CC1=CC=CC(N(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)C=2C=C(C)C=CC=2)=C1 SPDPTFAJSFKAMT-UHFFFAOYSA-N 0.000 description 4
- 229910045601 alloy Inorganic materials 0.000 description 4
- 239000000956 alloy Substances 0.000 description 4
- 230000000903 blocking effect Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 4
- 0 *c1cccc2c1c(C(F)(F)F)ccc2 Chemical compound *c1cccc2c1c(C(F)(F)F)ccc2 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 3
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- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
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- 238000000576 coating method Methods 0.000 description 3
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- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 3
- WQONPSCCEXUXTQ-UHFFFAOYSA-N 1,2-dibromobenzene Chemical compound BrC1=CC=CC=C1Br WQONPSCCEXUXTQ-UHFFFAOYSA-N 0.000 description 2
- DLXBGTIGAIESIG-UHFFFAOYSA-N 1,8-dibromonaphthalene Chemical compound C1=CC(Br)=C2C(Br)=CC=CC2=C1 DLXBGTIGAIESIG-UHFFFAOYSA-N 0.000 description 2
- PJZDEYKZSZWFPX-UHFFFAOYSA-N 2,6-dibromonaphthalene Chemical compound C1=C(Br)C=CC2=CC(Br)=CC=C21 PJZDEYKZSZWFPX-UHFFFAOYSA-N 0.000 description 2
- QYNTUCBQEHUHCS-UHFFFAOYSA-N 4-n-(3-methylphenyl)-1-n-[4-[4-(n-[4-(n-(3-methylphenyl)anilino)phenyl]anilino)phenyl]phenyl]-1-n,4-n-diphenylbenzene-1,4-diamine Chemical compound CC1=CC=CC(N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C(C)C=CC=2)=C1 QYNTUCBQEHUHCS-UHFFFAOYSA-N 0.000 description 2
- ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 9-bromoanthracene Chemical compound C1=CC=C2C(Br)=C(C=CC=C3)C3=CC2=C1 ZIRVQSRSPDUEOJ-UHFFFAOYSA-N 0.000 description 2
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- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 2
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- 239000011135 tin Substances 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000012780 transparent material Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 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
- 229910052727 yttrium Inorganic materials 0.000 description 1
- VWQVUPCCIRVNHF-UHFFFAOYSA-N yttrium atom Chemical compound [Y] VWQVUPCCIRVNHF-UHFFFAOYSA-N 0.000 description 1
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- H10K50/15—Hole transporting layers
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- C07C15/20—Polycyclic condensed hydrocarbons
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/10—Apparatus or processes specially adapted to the manufacture of electroluminescent light sources
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- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
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- H10K50/14—Carrier transporting layers
- H10K50/16—Electron transporting layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K50/17—Carrier injection layers
- H10K50/171—Electron injection layers
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
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- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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- C07C2603/02—Ortho- or ortho- and peri-condensed systems
- C07C2603/04—Ortho- or ortho- and peri-condensed systems containing three rings
- C07C2603/22—Ortho- or ortho- and peri-condensed systems containing three rings containing only six-membered rings
- C07C2603/24—Anthracenes; Hydrogenated anthracenes
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- C09K2211/1011—Condensed systems
Definitions
- the present invention provides a compound represented by the following formula (1).
- Ar 1 is phenyl or naphthyl
- Ar 2 is phenyl or naphthyl
- Ar 3 is hydrogen
- Ar 4 is unsubstituted or anthracenylene substituted with phenyl
- Ar 5 is naphthyl; Biphenyl; Or phenyl unsubstituted or substituted with naphthyl.
- Step 1-2 is a step of preparing a compound represented by Formula 1-6 by replacing the Br group of the compound represented by Formula 1-5 with B (OH) 2 groups.
- Tetrahydrofuran may be used as a solvent, and n-butyllithium and triethyl borate may be added and reacted, respectively.
- Step 2-3 is a step of preparing a compound represented by Chemical Formula 2-6 by reacting a compound represented by Chemical Formula 2-5 with bromine.
- the solvent may be chloroform.
- Step 2-5 is a step of preparing a compound represented by Chemical Formula 2-10 by reacting the compound represented by Chemical Formula 2-8 with the compound represented by Chemical Formula 2-9.
- Tetrahydrofuran may be used as the solvent, and tetrakis (triphenylphosphine) palladium (0) may be used together with a 2-normal potassium carbonate aqueous solution as a catalyst.
- the substrate functions as a support layer during the fabrication of the organic electroluminescent device and as a protective layer for construction of the device.
- a support layer during the fabrication of the organic electroluminescent device and as a protective layer for construction of the device.
- flatness and mechanical strength, thermal stability to withstand various processes, no volatile emissions, air and moisture ingress and transparency are required.
- a device having a high reflectance may be used for a device requiring a cathode direction or side light emission.
- Transparent materials include glass, quartz, and transparent resin films.
- the organic electroluminescent device is sufficiently transparent in the emission wavelength region of the device.
- the transparent electrode is set to use the above-mentioned conductive material and to ensure a predetermined light transmittance by a method such as vapor deposition or sputtering. It is preferable that the electrode of a light emitting surface has a light transmittance of 10% or more.
- a light emitting material or a dopant material which can be used for the light emitting layer together with the compound represented by the formula (1) of the present invention for example, anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, chrysene, fluorescein, perylene , Phthaloperylene, phthaloperylene, perinone, phthaloperinone, naphthaloperin, diphenylbutadiene, tetraphenylbutadiene, coumarin, oxadiazole, aldazine, bisbenzoxazolin, Bisstyryl, pyrazine, cyclopentadiene, quinoline metal complex, aminoquinoline metal complex, benzoquinoline metal complex, imine, diphenylethylene, vinylanthracene, diaminocarbazole, pyran, thiopyran, polymethine, melococyanine
- the hole transporting layer organic monomolecular material since the hole transporting layer organic monomolecular material has to have a fast hole transporting speed and forms an interface in contact with the light emitting layer, the ionization potential has an appropriate value between the hole injection layer and the light emitting layer in order to suppress the generation of the hole transporting layer and the light emitting layer interface excitation. The ability to properly control the electrons being moved is needed.
- an inorganic compound layer may be disposed between the light emitting layer and the electrode in order to improve charge injection property.
- alkali metal compound a fluoride, oxide, etc.
- an alkaline earth metal compound specifically, there may be mentioned LiF, Li 2 O, BaO, SrO, BaF 2, SrF 2 and the like.
- the resin that can be used examples include insulating resins such as polystyrene, polycarbonate, polyarylate, polyester, polyamide, polyurethane, polysulfone, polymethyl methacrylate, polymethyl acrylate, cellulose, and copolymers thereof; Photoconductive resins such as poly- N -vinylcarbazole and polysilane; And conductive resins such as polythiophene and polypyrrole. Moreover, antioxidant, an ultraviolet absorber, a plasticizer etc. are mentioned as an additive.
- FIG. 6 shows a 1 H-NMR graph of Example 3.
- the compound of Example 3 was prepared by the following preparation method.
- Example 40-48 was prepared using the same method as Example 3, using Intermediates 3-1 and 3-6, which correspond to the structures of Tables 10 and 11, respectively.
- the compound of Example 49 was prepared by the following preparation method.
- 1,8-dibromonaphthalene 50 g, 170 mmol
- phenylboronic acid 49 g, 400 mmol
- tetrakis (triphenylphosphine) palladium (0) 10 mmol
- 2-normal potassium carbonate aqueous solution was added thereto, followed by reflux for 24 hours.
- the mixture was extracted with ethyl acetate and the organic layer was dried over anhydrous magnesium sulfate, and then purified through a hexane column to obtain intermediate 51-1 in a yield of 71% (35 g).
- a substrate cut to ITO (indium tin oxide) transparent electrode having a thickness of 100 nm to a size of 40 mm ⁇ 40 mm ⁇ 0.7 mm was ultrasonically cleaned in distilled water in a detergent for 10 minutes, and then washed in distilled water for 10 minutes. Washing was repeated several times.
- ITO indium tin oxide
- Example 3 having a thickness of 30 nm and a compound having the following structural formula were simultaneously formed on the NPB film at a weight ratio of 100 to 5 to form a light emitting layer film having a thickness of 30 nm.
- An organic electroluminescent device was manufactured in the same manner as in Experimental Example 1, except that Examples 6, 7, 8, 23, and 39 were used as light emitting materials instead of the compounds of Example 3, and the results were measured.
- An organic electroluminescent device was manufactured in the same manner as in Experiment 1 except for using Examples 51, 52, 53, 54, 57, 59, 64, and 88 as light emitting materials, respectively, in place of the compound of Example 3. The result was measured.
- An organic electroluminescent device was manufactured in the same manner as in Experiment 1, except that Compound AN having the following structural formula as a light emitting material was used instead of the compound of Example 3.
- the current density was 75.3 mA / cm 2
- the luminous efficiency of this device was measured to be 4.87 cd / A at 7V, which was calculated as conversion efficiency (luminescence efficiency / y) and found to be 34.3.
- An organic electroluminescent device was manufactured in the same manner as in Experiment 1, except that Compound ADN having the following structural formula was used as a light emitting material instead of Compound AN used in Experimental Example 5.
- the embodiment of the present invention can be confirmed that the luminous efficiency and life is superior to the comparative example.
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Abstract
Description
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
4 | δ 7.12~7.22(m, 6H), 7.25~7.31(m, 7H), 7.39~7.43(m, 2H), 7.46~7.54(m, 3H), 7.56~7.68(m, 7H), 7.69~7.71(t, 1H), 7.99~8.01(m, 3H), 8.02~8.05(d, 1H) | |
5 | δ 7.17~7.22(m, 4H), 7.27~7.51(m, 7H), 7.54~7.62(m, 7H), 7.64~7.80(m, 3H), 7.85~7.96(m, 5H), 7.98~8.01(m, 2H), 7.96~8.02(d, 2H) | |
6 | δ 7.18~7.22(m, 8H), 7.22~7.41(m, 7H), 7.54~7.67(m, 5H), 7.69~7.78(m, 4H), 7.81~7.92(m, 6H), 8.01~8.04(d, 2H) | |
7 | δ 7.11~7.22(m, 7H), 7.23~7.27(m, 10H), 7.34~7.36(m, 2H), 7.46~7.54(m, 3H), 7.54~7.66(m, 5H), 7.68~7.72(m, 2H), 7.98~8.02(m, 3H), 8.04~8.07(d, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
8 | δ 7.21~7.25(m, 8H), 7.25~7.47(m, 7H), 7.58~7.63(m, 7H), 7.69~7.82(m, 3H), 7.88~7.94(m, 5H), 7.99~8.01(m, 2H), 8.03~8.06(d, 2H) | |
9 | δ 7.14~7.22(m, 2H), 7.25~7.31(m, 7H), 7.39~7.43(m, 6H), 7.46~7.54(m, 3H), 7.56~7.68(m, 6H), 7.69~7.71(m, 2H), 7.99~8.01(m, 2H), 8.02~8.05(d, 2H) | |
10 | δ 7.19~7.24(m, 2H), 7.32~7.44(m, 7H), 7.48~7.71(m, 11H), 7.75~7.83(m, 3H), 7.86~7.92(m, 7H), 8.04~8.08(d, 2H) | |
11 | δ 7.17~7.45(m, 9H), 7.49~7.66(m, 9H), 7.69~7.76(m, 3H), 7.83~7.99(m, 7H), 8.01~8.03(d, 2H), 8.07~8.10(d, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
12 | δ 7.13~7.49(m, 13H), 7.51~7.68(m, 9H), 7.72~7.79(m, 5H), 7.86~7.94(m, 5H), 7.96~8.02(m, 2H), 8.08~8.11(d, 2H) | |
13 | δ 7.12~7.47(m, 13H), 7.51~7.68(m, 9H), 7.72~7.79(m, 3H), 7.86~7.94(m, 5H), 7.96~8.02(m, 2H), 8.03~8.06(d, 2H), 8.08~8.11(d, 2H) | |
14 | δ 7.12~7.24(m, 4H), 7.32~7.47(m, 8H), 7.51~7.68(m, 9H), 7.72~7.79(m, 3H), 7.86~7.94(m, 6H), 7.96~8.02(m, 2H), 8.08~8.11(d, 2H) | |
15 | δ 7.22~7.29(m, 3H), 7.31~7.37(m, 4H), 7.39~7.48(m, 5H), 7.51~7.67(m, 6H), 7.72~7.84(m, 5H), 7.86~7.92(m, 5H), 8.02~8.05(d, 2H) | |
16 | δ 7.22~7.29(m, 3H), 7.31~7.37(m, 4H), 7.39~7.48(m, 5H), 7.51~7.67(m, 7H), 7.72~7.84(m, 6H), 7.86~7.92(m, 5H), 8.02~8.05(d, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
17 | δ 7.31~7.48(m, 7H), 7.53~7.65(m, 9H), 7.72~7.82(m, 5H), 7.85~7.92(m, 7H), 7.95~8.01(m, 2H), 8.02~8.05(d, 2H) | |
18 | δ 7.16~7.25(m, 4H), 7.30~7.43(m, 8H), 7.51~7.66(m, 10H), 7.75~7.84(m, 6H), 7.86~7.92(m, 6H), 8.02~8.05(d, 2H) | |
19 | δ 7.18~7.28(m, 4H), 7.34~7.48(m, 7H), 7.57~7.68(m, 9H), 7.72~7.84(m, 5H), 7.86~7.92(m, 7H), 7.99~8.01(m, 2H), 8.02~8.05(d, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
20 | δ 7.18~7.24(m, 4H), 7.30~7.44(m, 6H), 7.48~7.52(m, 5H), 7.55~7.67(m, 7H), 7.75~7.84(m, 6H), 7.86~7.92(m, 4H), 8.01~8.04(m, 2H) | |
21 | δ 7.13~7.26(m, 2H), 7.33~7.42(m, 2H), 7.48~7.57(m, 5H), 7.64~7.79(m, 7H), 7.82~7.94(m, 6H), 8.03~8.09(m, 2H) | |
22 | δ 7.13~7.26(m, 2H), 7.33~7.46(m, 3H), 7.51~7.62(m, 6H), 7.69~7.82(m, 7H), 7.84~7.96(m, 6H), 8.03~8.09(m, 2H) | |
23 | δ 7.18~7.27(m, 2H), 7.35~7.45(m, 4H), 7.53~7.65(m, 7H), 7.75~7.83(m, 4H), 7.84~7.90(m, 5H), 7.94~8.02(m, 2H), 8.04~8.10(m, 2H) | |
24 | δ 7.13~7.26(m, 4H), 7.33~7.46(m, 5H), 7.51~7.62(m, 6H), 7.69~7.82(m, 7H), 7.84~7.96(m, 6H), 8.03~8.09(m, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
25 | δ 7.15~7.27(m, 4H), 7.34~7.48(m, 6H), 7.56~7.65(m, 7H), 7.72~7.81(m, 4H), 7.87~7.92(m, 5H), 7.96~8.04(m, 2H), 8.07~8.12(m, 2H) | |
26 | δ 7.18~7.27(m, 4H), 7.39~7.56(m, 10H), 7.61~7.66(m, 4H), 7.75~7.81(m, 4H), 7.84~7.91(m, 4H), 8.04~8.10(m, 2H) | |
27 | δ 7.31~7.43(m, 4H), 7.45~7.57(m, 7H), 7.59~7.73(m, 6H), 7.75~7.83(m, 5H), 7.91~7.97(m, 2H), 8.02~8.10(m, 2H), 8.14~8.20(m, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
28 | δ 7.27~7.42(m, 4H),7.50~7.64(m, 6H), 7.67~7.76(m, 9H), 7.77~7.82(m, 4H), 7.87~7.98(m, 5H), 8.13~8.20(m, 2H) | |
29 | δ 7.30~7.44(m, 4H),7.50~7.63(m, 7H), 7.69~7.80(m, 10H), 7.85~7.97(m, 5H), 8.03~8.09(m, 2H), 8.17~8.23(m, 2H) | |
30 | δ 7.19~7.26(m, 4H), 7.33~7.48(m, 8H), 7.54~7.83(m, 15H), 7.84~7.95(m, 5H), 8.19~8.24(m, 2H) | |
31 | δ 7.18~7.25(m, 4H), 7.37~7.51(m, 8H), 7.57~7.82(m, 13H), 7.86~7.97(m, 5H), 8.04~8.11(m, 2H), 8.19~8.24(m, 2H) | |
32 | δ 7.20~7.26(m, 4H), 7.37~7.53(m, 11H), 7.59~7.77(m, 7H), 7.78~7.85(m, 4H), 7.89~7.93(m, 2H), 8.03~8.11(m, 2H), 8.18~8.22(m, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
33 | δ 7.32~7.46(m, 6H), 7.58~7.65(m, 4H), 7.71~7.86(m, 6H), 7.93~8.02(m, 2H), 8.23~8.34(m, 4H), 8.57~8.66(m, 2H) | |
34 | δ 7.27~7.38(m, 3H), 7.48~7.70(m, 8H), 7.70~7.82(m, 6H), 7.87~7.96(m, 3H), 8.20~8.32(m, 4H), 8.53~8.64(m, 2H) | |
35 | δ 7.32~7.42(m, 3H), 7.61~7.83(m, 12H), 7.87~7.93(m, 2H), 7.94~8.06(m, 3H), 8.22~8.33(m, 4H), 8.57~8.67(m, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
36 | δ 7.18~7.23(m, 4H), 7.33~7.41(m, 3H), 7.53~7.74(m, 8H), 7.76~7.82(m, 6H), 7.89~8.00(m, 3H), 8.22~8.33(m, 4H), 8.58~8.67(m, 2H) | |
37 | δ 7.20~7.26(m, 4H), 7.37~7.45(m, 3H), 7.56~7.79(m, 12H), 7.85~7.91(m, 2H), 7.94~8.04(m, 3H), 8.24~8.36(m, 4H), 8.62~8.71(m, 2H) | |
38 | δ 7.22~7.28(m, 4H), 7.39~7.49(m, 6H), 7.58~7.65(m, 4H), 7.74~7.88(m, 6H), 7.94~8.04(m, 2H), 8.27~8.37(m, 4H), 8.60~8.70(m, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
40 | δ 7.31~7.39(m, 3H), 7.45~7.68(m, 8H), 7.72~7.85(m, 6H), 7.88~8.05(m, 5H), 8.20~8.29(m, 2H) | |
41 | δ 7.32~7.44(m, 4H), 7.47~7.58(m, 5H), 7.62~7.80(m, 8H), 7.85~7.97(m, 5H), 8.04~8.16(m, 2H), 8.18~8.26(m, 2H) | |
42 | δ 7.21~7.30(m, 4H), 7.34~7.44(m, 2H), 7.45~7.56(m, 7H), 7.61~7.84(m, 10H), 7.88~8.03(m, 5H), 8.18~8.27(m, 2H) | |
43 | δ 7.18~7.28(m, 4H), 7.32~7.44(m, 3H), 7.47~7.58(m, 6H), 7.64~7.82(m, 8H), 7.86~7.99(m, 5H), 8.02~8.18(m, 2H), 8.20~8.30(m, 2H) | |
44 | δ 7.22~7.31(m, 4H), 7.35~7.47(m, 6H), 7.53~7.78(m, 12H), 7.82~7.96(m, 4H), 8.22~8.33(m, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
45 | δ 7.24~7.49(m, 11H), 7.54~7.73(m, 11H), 7.85~7.94(m, 4H), 8.19~8.29(m, 3H), 8.41~8.51(m, 3H) | |
46 | δ 7.26~7.46(m, 8H), 7.58~7.78(m, 13H), 7.83~7.93(m, 5H), 8.04~8.15(m, 2H), 8.22~8.33(m, 3H), 8.42~8.51(m, 3H) | |
47 | δ 7.23~7.45(m, 9H), 7.56~7.77(m, 9H), 7.88~7.95(m, 4H), 8.27~8.39(m, 4H) | |
48 | δ 7.27~7.48(m, 6H), 7.54~7.72(m, 11H), 7.86~7.95(m, 5H), 8.01~8.13(m, 2H), 8.25~8.38(m, 4H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
52 | δ 7.24~7.56(m, 11H), 7.59~7.71(m, 7H), 7.74~7.80(m, 4H), 7.85~7.91(m, 4H), 8.28~8.32(m, 2H), 8.35~8.41(m, 2H) | |
53 | δ 7.31~7.51(m, 9H), 7.53~7.64(m, 7H), 7.72~7.84(m, 6H), 7.86~7.92(m, 4H), 7.98~8.04(m, 2H), 8.35~8.41(m, 2H) | |
54 | δ 7.19~7.50(m, 17H), 7.60~7.69(m, 5H), 7.76~7.82(m, 4H), 7.88~7.93(m, 4H), 8.30~8.34(m, 2H), 8.36~8.41(m, 2H) | |
55 | δ 7.20~7.26(m, 4H), 7.34~7.48(m, 11H), 7.54~7.62(m, 5H), 7.70~7.81(m, 5H), 7.85~7.93(m, 5H), 7.99~8.03(m, 2H), 8.35~8.40(m, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
56 | δ 7.22~7.27(m, 4H), 7.38~7.51(m, 14H), 7.58~7.61(m, 2H), 7.72~7.83(m, 6H), 7.86~7.93(m, 4H), 8.37~8.41(m, 2H) | |
57 | δ 7.24~7.53(m, 17H), 7.59~7.70(m, 5H), 7.72~7.81(m, 3H), 7.83~7.94(m, 5H), 8.35~8.44(m, 4H) | |
58 | δ 7.22~7.25(m, 4H), 7.33~7.45(m, 9H), 7.47~7.60(m, 7H), 7.65~7.78(m, 5H), 7.84~7.92(m, 5H), 8.01~8.04(m, 2H), 8.34~8.40(m, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
59 | δ 7.23~7.50(m, 21H), 7.60~7.71(m, 5H), 7.69~7.81(m, 4H), 7.85~7.93(m, 4H), 8.35~8.44(m, 4H) | |
60 | δ 7.23~7.27(m, 8H), 7.36~7.49(m, 11H), 7.54~7.62(m, 5H), 7.69~7.81(m, 5H), 7.85~7.93(m, 5H), 7.99~8.03(m, 2H), 8.35~8.40(m, 2H) | |
61 | δ 7.22~7.27(m, 8H), 7.36~7.52(m, 14H), 7.56~7.62(m, 2H), 7.71~7.83(m, 6H), 7.86~7.94(m, 4H), 8.35~8.40(m, 2H) | |
62 | δ 7.21~7.56(m, 16H), 7.59~7.65(m, 4H), 7.69~7.81(m, 6H), 7.85~7.92(m, 4H), 8.37~8.52(m, 4H) | |
63 | δ 7.21~7.34(m, 6H), 7.36~7.51(m, 9H), δ 7.56~7.64(m, 7H), 7.72~7.83(m, 4H), 7.87~7.91(m, 4H), 8.31~8.46(m, 6H) | |
64 | δ 7.19~7.32(m, 6H), 7.34~7.50(m, 7H), 7.54~7.63(m, 7H), 7.71~7.83(m, 5H), 7.85~7.93(m, 5H), 7.98~8.03(m, 2H), 8.35~8.51(m, 4H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
65 | δ 7.20~7.54(m, 19H), 7.58~7.68(m, 7H), 7.75~7.85(m, 4H), 7.88~7.92(m, 4H), 8.32~8.46(m, 6H) | |
66 | δ 7.21~7.52(m, 17H), 7.56~7.65(m, 7H), 7.70~7.83(m, 5H), 7.86~7.94(m, 5H), 7.99~8.03(m, 2H), 8.35~8.51(m, 4H) | |
67 | δ 7.20~7.55(m, 20H), 7.58~7.64(m, 4H), 7.68~7.81(m, 6H), 7.85~7.92(m, 4H), 8.37~8.52(m, 4H) | |
68 | δ 7.23~7.26(m, 2H), 7.34~7.57(m, 12H), 7.60~7.68(m, 4H), 7.72~7.85(m, 8H), 7.88~7.96(m, 6H), 8.37~8.49(m, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
69 | δ 7.32~7.52(m, 13H), 7.58~7.82(m, 13H), 7.86~7.94(m, 6H), 8.37~8.52(m, 4H) | |
70 | δ 7.36~7.52(m, 11H), 7.56~7.66(m, 7H), 7.71~7.82(m, 7H), 7.84~7.92(m, 7H), 8.00~8.04(m, 2H), 8.40~8.51(m, 2H) | |
71 | δ 7.21~7.54(m, 17H), 7.58~7.82(m, 13H), 7.86~7.94(m, 6H), 8.37~8.52(m, 4H) | |
72 | δ 7.24~7.27(m, 4H), 7.35~7.52(m, 11H), 7.56~7.65(m, 7H), 7.70~7.83(m, 7H), 7.86~7.94(m, 7H), 7.99~8.03(m, 2H), 8.40~8.51(m, 2H) | |
73 | δ 7.23~7.26(m, 4H), 7.34~7.55(m, 14H), 7.58~7.65(m, 4H), 7.71~7.85(m, 8H), 7.87~7.96(m, 6H), 8.38~8.49(m, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
74 | δ 7.21~7.31(m, 5H), 7.37~7.57(m, 8H), 7.61~7.73(m, 7H), 7.76~7.81(m, 4H), 7.85~7.94(m, 3H), 8.12~8.14(s, 1H), 8.41~8.52(m, 4H) | |
75 | δ 7.23~7.32(m, 5H), 7.34~7.55(m, 9H), 7.58~7.69(m, 8H), 7.76~7.81(m, 4H), 7.86~7.97(m, 3H), 8.11~8.13(s, 1H), 8.40~8.52(m, 4H) | |
76 | δ 7.32~7.56(m, 12H), 7.58~7.66(m, 8H), 7.70~7.82(m, 5H), 7.88~8.04(m, 5H), 8.08~8.15(m, 2H), 8.42~8.51(m, 2H) | |
77 | δ 7.23~7.54(m, 18H), 7.58~7.69(m, 8H), 7.76~7.81(m, 4H), 7.86~7.97(m, 3H), 8.11~8.13(s, 1H), 8.40~8.52(m, 4H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
78 | δ 7.22~7.26(m, 4H), 7.35~7.56(m, 12H), 7.58~7.66(m, 8H), 7.70~7.82(m, 5H), 7.88~8.04(m, 5H), 8.08~8.15(m, 2H), 8.42~8.51(m, 2H) | |
79 | δ 7.23~7.26(m, 4H), 7.34~7.56(m, 15H), 7.58~7.67(m, 5H), 7.71~7.84(m, 6H), 7.88~7.96(m, 4H), 8.41~8.50(m, 2H) | |
80 | δ 7.32~7.49(m, 10H), 7.54~7.60(m, 2H), 7.70~7.81(m, 8H), 7.97~8.10(m, 2H), 8.32~8.48(m, 4H), 8.76~8.91(m, 2H) | |
81 | δ 7.26~7.50(m, 9H), 7.59~7.83(m, 11H), 7.95~8.01(m, 2H), 8.29~8.47(s, 6H), 8.76~8.90(m, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
82 | δ 7.30~7.48(m, 7H), 7.54~7.62(m, 5H), 7.67~7.82(m, 7H), 7.95~8.15(m, 5H), 8.34~8.49(m, 4H), 8.76~8.91(m, 2H) | |
83 | δ 7.22~7.51(m, 13H), 7.58~7.82(m, 11H), 7.96~8.01(m, 2H), 8.31~8.50(s, 6H), 8.78~8.91(m, 2H) | |
84 | δ 7.23~7.26(m, 4H), 7.32~7.50(m, 7H), 7.56~7.64(m, 5H), 7.69~7.83(m, 7H), 7.94~8.14(m, 5H), 8.34~8.49(m, 4H), 8.76~8.91(m, 2H) | |
85 | δ 7.23~7.26(m, 4H), 7.34~7.51(m, 10H), 7.57~7.62(m, 2H), 7.73~7.82(m, 8H), 7.99~8.11(m, 2H), 8.33~8.49(m, 4H), 8.76~8.91(m, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
87 | δ 7.31~7.51(m, 9H), 7.58~7.82(m, 13H), 7.89~7.94(m, 2H), 7.98~8.08(m, 2H), 8.31~8.46(m, 4H) | |
88 | δ 7.33~7.52(m, 8H), 7.56~7.63(m, 4H), 7.67~7.83(m, 9H), 7.92~8.13(m, 7H), 8.31~8.45(m, 2H) | |
89 | δ 7.23~7.52(m, 13H), 7.58~7.82(m, 13H), 7.89~7.93(m, 2H), 7.97~8.06(m, 2H), 8.32~8.46(m, 4H) | |
90 | δ 7.23~7.26(m, 4H), 7.34~7.50(m, 7H), 7.54~7.62(m, 5H), 7.68~7.82(m, 9H), 7.94~8.14(m, 7H), 8.31~8.45(m, 2H) | |
91 | δ 7.22~7.27(m, 4H), 7.36~7.52(m, 10H), 7.57~7.62(m, 2H), 7.69~7.84(m, 10H), 7.94~8.14(m, 4H), 8.32~8.45(m, 2H) |
실시예번호 | 화학구조 | 1H NMR (CDCl3, 200 MHz) |
92 | δ 7.30~7.52(m, 12H), 7.57~7.71(m, 13H), 7.87~7.94(m, 5H), 7.99~8.07(m, 2H), 8.37~8.43(m, 2H), 8.46~8.57(m, 4H) | |
93 | δ 7.32~7.50(m, 12H), 7.57~7.81(m, 13H), 7.89~7.93(m, 5H), 7.99~8.06(m, 2H), 8.40~8.52(m, 6H) | |
94 | δ 7.30~7.51(m, 10H), 7.55~7.79(m, 11H), 7.89~7.93(m, 5H), 7.99~8.06(m, 2H), 8.40~8.52(m, 4H) | |
95 | δ 7.32~7.50(m, 10H), 7.57~7.81(m, 11H), 7.87~7.92(m, 5H), 7.99~8.06(m, 2H), 8.41~8.53(m, 4H) |
호스트물질 | 도판트물질 | 전기발광(nm)(EL) | 발광효율(cd/A)@ 7V | 환산효율(발광효율/CIEy) | 색좌표 @ 7V | 수명1000cd/m2 | |
CIEx | CIEy | ||||||
실시예 3 | BD | 461 | 4.93 | 35.0 | 0.148 | 0.141 | 93% |
실시예 4 | 462 | 5.39 | 38.0 | 0.146 | 0.142 | 113% | |
실시예 6 | 461 | 5.22 | 36.0 | 0.147 | 0.145 | 108% | |
실시예 7 | 463 | 5.53 | 39.2 | 0.145 | 0.141 | 112% | |
실시예 9 | 460 | 4.88 | 33.4 | 0.145 | 0.146 | 92% | |
실시예 23 | 461 | 5.12 | 36.8 | 0.145 | 0.139 | 98% | |
실시예 39 | 462 | 5.42 | 36.4 | 0.146 | 0.149 | 107% | |
AN | 460 | 4.87 | 34.3 | 0.151 | 0.142 | 100% | |
ADN | 462 | 4.80 | 33.1 | 0.143 | 0.145 | 91% |
호스트물질 | 도판트물질 | 전기발광(nm)(EL) | 발광효율(cd/A)@ 7V | 환산효율(발광효율/CIEy) | 색좌표 @ 7V | 수명1000cd/m2 | |
CIEx | CIEy | ||||||
실시예 51 | BD | 462 | 5.12 | 36.3 | 0.146 | 0.141 | 91% |
실시예 | 461 | 5.34 | 37.3 | 0.144 | 0.143 | 110% | |
실시예 | 461 | 5.36 | 37.2 | 0.145 | 0.144 | 103% | |
실시예 | 462 | 5.42 | 38.7 | 0.144 | 0.140 | 112% | |
실시예 | 462 | 5.24 | 37.7 | 0.145 | 0.139 | 117% | |
실시예 | 461 | 5.35 | 40.2 | 0.143 | 0.133 | 98% | |
실시예 | 462 | 5.17 | 36.7 | 0.145 | 0.141 | 93% | |
실시예 | 462 | 5.23 | 38.2 | 0.147 | 0.137 | 111% | |
ADN | 462 | 4.80 | 33.1 | 0.143 | 0.145 | 100% |
Claims (19)
- 하기 화학식 1로 표시되는 화합물:[화학식 1]상기 식에서,Ar1은 수소 또는 C6-10 1가 방향족기이고, 상기 C6-10 1가 방향족기는 비치환되거나, 페닐 또는 나프틸로 치환되고,Ar2는 수소 또는 C6-10 1가 방향족기이고. 상기 C6-10 1가 방향족기는 비치환되거나, 페닐 또는 나프틸로 치환되고,Ar3은 수소 또는 C6-10 1가 방향족기이고. 상기 C6-10 1가 방향족기는 비치환되거나, 페닐 또는 나프틸로 치환되고,Ar4는 C6-16 2가 방향족기이고, 상기 C6-16 2가 방향족기는 비치환되거나 페닐로 치환되고, 및Ar5는 C6-14 1가 방향족기이고, 상기 C6-14 1가 방향족기는 비치환되거나, 나프틸, 페닐, 나프틸로 치환된 페닐, 또는 비페닐로 치환되고,단, Ar3이 C6-10 1가 방향족기인 경우, Ar1 및 Ar2는 각각 수소이고, Ar3이 수소인 경우, Ar1 및 Ar2는 각각 C6-10 1가 방향족기이다.
- 제1항에 있어서,상기 Ar1 및 상기 Ar2는 각각 수소이고,상기 Ar3은 페닐; 또는 비치환되거나, 페닐 또는 나프틸로 치환된 나프틸이고,상기 Ar4는 나프틸렌; 페닐렌; 피레닐렌; 페난트릴렌; 또는 비치환되거나, 페닐로 치환된 안트라세닐렌이고, 및상기 Ar5는 나프틸; 비페닐; 비치환되거나, 나프틸로 치환된 페닐; 또는 비치환되거나 나프틸, 페닐, 나프틸로 치환된 페닐, 또는 비페닐로 치환된 안트라세닐인 화합물.
- 제1항에 있어서,상기 Ar1 및 상기 Ar2는 각각 수소이고,상기 Ar3은 비치환되거나, 페닐 또는 나프틸로 치환된 나프틸이고,상기 Ar4는 나프틸렌, 또는 안트라세닐렌이고, 및상기 Ar5는 나프틸; 페닐; 또는 나프틸, 또는 페닐로 치환된 안트라세닐인 화합물.
- 제1항에 있어서,상기 Ar1 및 상기 Ar2는 각각 수소이고,상기 Ar3은 페닐이고,상기 Ar4는 페닐렌이고, 및상기 Ar5는 나프틸; 페닐; 나프틸로 치환된 페닐; 또는 비페닐로 치환된 안트라세닐인 화합물.
- 제1항에 있어서,상기 Ar1 및 상기 Ar2는 각각 수소이고,상기 Ar3은 페닐이고,상기 Ar4는 피렌닐; 또는 페난트릴렌이고, 및상기 Ar5는 나프틸; 비페닐; 또는 비치환되거나 나프틸로 치환된 페닐인 화합물.
- 제1항에 있어서,상기 Ar1 및 상기 Ar2는 각각 수소이고,상기 Ar3은 페닐 또는 나프틸이고,상기 Ar4는 비치환되거나, 페닐로 치환된 안트라세닐렌이고, 및상기 Ar5는 나프틸; 비페닐; 또는 비치환되거나, 나프틸로 치환된 페닐인 화합물.
- 제1항에 있어서,상기 Ar1 및 상기 Ar2는 각각 수소이고, 및상기 Ar3은 페닐; 1-나프틸; 2-나프틸; 6-페닐-2-나프틸; 또는 6-(1-나프틸)-2-나프틸인 화합물.
- 제1항에 있어서,상기 Ar1은 페닐; 또는 비치환되거나, 페닐 또는 나프틸로 치환된 나프틸이고,상기 Ar2는 페닐; 또는 비치환되거나, 페닐 또는 나프틸로 치환된 나프틸이고,상기 Ar3은 수소이고,상기 Ar4는 나프틸렌; 페닐렌; 피레닐렌; 페난트릴렌; 또는 비치환되거나, 페닐로 치환된 안트라세닐렌이고, 및상기 Ar5는 나프틸; 비페닐; 비치환되거나, 나프틸로 치환된 페닐; 또는 비치환되거나 나프틸, 페닐, 나프틸로 치환된 페닐, 또는 비페닐로 치환된 안트라세닐인 화합물.
- 제1항에 있어서,상기 Ar1은 비치환되거나, 페닐 또는 나프틸로 치환된 나프틸이고,상기 Ar2는 비치환되거나, 페닐 또는 나프틸로 치환된 나프틸이고,상기 Ar3은 수소이고,상기 Ar4는 나프틸렌 또는 안트라세닐렌이고, 및상기 Ar5는 나프틸; 페닐; 또는 나프틸, 또는 페닐로 치환된 안트라세닐인 화합물.
- 제1항에 있어서,상기 Ar1은 페닐이고,상기 Ar2는 페닐이고,상기 Ar3은 수소이고,상기 Ar4는 페닐렌이고, 및상기 Ar5는 나프틸; 페닐; 나프틸로 치환된 페닐; 또는 비페닐로 치환된 안트라세닐인 화합물.
- 제1항에 있어서,상기 Ar1은 페닐이고,상기 Ar2는 페닐이고,상기 Ar3은 수소이고,상기 Ar4는 피렌닐 또는 페난트릴렌이고, 및상기 Ar5는 나프틸; 비페닐; 또는 비치환되거나, 나프틸로 치환된 페닐인 화합물.
- 제1항에 있어서,상기 Ar1은 페닐 또는 나프틸이고,상기 Ar2는 페닐 또는 나프틸이고,상기 Ar3은 수소이고,상기 Ar4는 비치환되거나, 페닐로 치환된 안트라세닐렌이고, 및상기 Ar5는 나프틸; 비페닐; 또는 비치환되거나, 나프틸로 치환된 페닐인 화합물.
- 제1항에 있어서,상기 Ar1 및 상기 Ar2는 각각 페닐; 1-나프틸; 2-나프틸; 6-페닐-2-나프틸; 또는 6-(1-나프틸)-2-나프틸이고, 및상기 Ar3은 수소인 화합물.
- 제1항에 있어서,상기 Ar1 및 Ar2는 페닐이고, 및상기 Ar3은 수소인 화합물.
- 제1항에 있어서,상기 Ar4는 1,4-나프틸렌; 2,6-나프틸렌; 1,4-페닐렌; 1,6-피레닐렌; 2,7-페난트릴렌; 9,10-안트라세닐렌; 또는 9-페닐-2,10-안트라세닐렌인 화합물.
- 제1항에 있어서,상기 Ar5는 1-나프틸; 2-나프틸; 비페닐-4-일; 페닐; 4-(1-나프틸)-페닐; 4-(2-나프틸)-페닐; 10-(1-나프틸)-9-안트라세닐; 10-(2-나프틸)-9-안트라세닐; 10-페닐-9-안트라세닐; 10-(4-(1-나프틸)페닐)-9-안트라세닐; 10-(4-(2-나프틸)페닐)-9-안트라세닐; 또는 10-(비페닐-4-일)-9-안트라세닐인 화합물.
- 제1항 내지 제17항 중 어느 한 항의 화합물로 이루어진 유기 전기 발광 소자용 재료.
- 음극과 양극 사이에 적어도 하나의 발광층을 포함하는 단층 또는 복수층으로 이루어지는 유기 박막층이 협지되어 있는 유기 전기발광 소자에 있어서,상기 유기 박막층의 적어도 1층이 제18항의 유기 전기 발광 소자용 재료를 함유하는 유기 전기 발광 소자.
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CN201280020856.4A CN103534331B (zh) | 2011-03-29 | 2012-03-29 | 萘衍生物、包括其的有机材料及包括其的有机电致发光元件 |
US14/008,576 US9024304B2 (en) | 2011-03-29 | 2012-03-29 | Naphthalene derivative, organic material including the same, and organic electroluminescent device including the same |
JP2014502471A JP2014522380A (ja) | 2011-03-29 | 2012-03-29 | ナフタレン誘導体、それを用いた有機材料、及びそれを用いた有機el素子 |
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JP2017054939A (ja) * | 2015-09-10 | 2017-03-16 | 株式会社東芝 | 有機光電変換素子、及び固体撮像素子 |
WO2017118174A1 (zh) * | 2016-01-07 | 2017-07-13 | 广州华睿光电材料有限公司 | 用于制备有机电子器件的有机功能化合物及其应用 |
CN109790459B (zh) * | 2016-11-23 | 2022-08-12 | 广州华睿光电材料有限公司 | 有机化合物 |
JP2020511006A (ja) * | 2017-03-01 | 2020-04-09 | メルク パテント ゲーエムベーハー | 有機エレクトロルミネッセント素子 |
CN110627601A (zh) * | 2018-06-22 | 2019-12-31 | 天津大学 | 有机光电半导体材料及其制备方法与应用 |
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US20140299849A1 (en) | 2014-10-09 |
CN103534331B (zh) | 2016-06-08 |
CN103534331A (zh) | 2014-01-22 |
WO2012134191A3 (ko) | 2013-01-10 |
US9024304B2 (en) | 2015-05-05 |
EP2692823A2 (en) | 2014-02-05 |
EP2692823A4 (en) | 2014-09-03 |
JP2014522380A (ja) | 2014-09-04 |
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