KR20070009304A - 전자 전달 화합물 및 그 유기전계발광소자 - Google Patents
전자 전달 화합물 및 그 유기전계발광소자 Download PDFInfo
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- KR20070009304A KR20070009304A KR1020050064458A KR20050064458A KR20070009304A KR 20070009304 A KR20070009304 A KR 20070009304A KR 1020050064458 A KR1020050064458 A KR 1020050064458A KR 20050064458 A KR20050064458 A KR 20050064458A KR 20070009304 A KR20070009304 A KR 20070009304A
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- South Korea
- Prior art keywords
- electron transport
- formula
- compound
- light emitting
- substituted
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- 239000000126 substance Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims abstract description 31
- -1 terpyridinyl Chemical group 0.000 claims abstract description 12
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims abstract description 11
- 125000003118 aryl group Chemical group 0.000 claims abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 7
- 239000004305 biphenyl Chemical group 0.000 claims abstract description 6
- 235000010290 biphenyl Nutrition 0.000 claims abstract description 6
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 6
- 150000002367 halogens Chemical group 0.000 claims abstract description 6
- 125000001424 substituent group Chemical group 0.000 claims abstract description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 5
- 125000002183 isoquinolinyl group Chemical group C1(=NC=CC2=CC=CC=C12)* 0.000 claims abstract description 4
- YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims abstract description 3
- 125000001931 aliphatic group Chemical group 0.000 claims abstract description 3
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 3
- 125000004076 pyridyl group Chemical group 0.000 claims abstract description 3
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims abstract description 3
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 claims abstract description 3
- 125000004625 phenanthrolinyl group Chemical group N1=C(C=CC2=CC=C3C=CC=NC3=C12)* 0.000 claims abstract 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 5
- 125000006325 2-propenyl amino group Chemical group [H]C([H])=C([H])C([H])([H])N([H])* 0.000 claims description 3
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 108090000407 Elongation factor 4 Proteins 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- NJTYYLDVWDGUSN-UHFFFAOYSA-N N,N-diphenylmorpholin-4-amine Chemical compound C1CN(CCO1)N(c1ccccc1)c1ccccc1 NJTYYLDVWDGUSN-UHFFFAOYSA-N 0.000 claims description 2
- 102100033095 Translation factor GUF1, mitochondrial Human genes 0.000 claims description 2
- 125000003282 alkyl amino group Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004104 aryloxy group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims 1
- 229910052731 fluorine Inorganic materials 0.000 claims 1
- 239000011737 fluorine Substances 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 14
- 238000002425 crystallisation Methods 0.000 abstract description 4
- 230000008025 crystallization Effects 0.000 abstract description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 abstract description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 14
- 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 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000758 substrate Substances 0.000 description 12
- 239000011521 glass Substances 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000011368 organic material Substances 0.000 description 6
- 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 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000000741 silica gel Substances 0.000 description 4
- 229910002027 silica gel Inorganic materials 0.000 description 4
- FDTFURCYZNFFNA-UHFFFAOYSA-N 1,6-dibromo-3,8-diphenylpyrene Chemical compound C12=C3C=4C=CC2=C(Br)C=C(C=2C=CC=CC=2)C1=CC=C3C(Br)=CC=4C1=CC=CC=C1 FDTFURCYZNFFNA-UHFFFAOYSA-N 0.000 description 3
- AYARQDPKFKTFCV-UHFFFAOYSA-N 1,6-diphenylpyrene Chemical compound C1=CC=CC=C1C1=CC=C(C=C2)C3=C4C2=C(C=2C=CC=CC=2)C=CC4=CC=C13 AYARQDPKFKTFCV-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000010405 anode material Substances 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 239000002019 doping agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- HXITXNWTGFUOAU-UHFFFAOYSA-N phenylboronic acid Chemical compound OB(O)C1=CC=CC=C1 HXITXNWTGFUOAU-UHFFFAOYSA-N 0.000 description 2
- 229910000027 potassium carbonate Inorganic materials 0.000 description 2
- 238000001953 recrystallisation Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
- JRCJYPMNBNNCFE-UHFFFAOYSA-N 1,6-dibromopyrene Chemical compound C1=C2C(Br)=CC=C(C=C3)C2=C2C3=C(Br)C=CC2=C1 JRCJYPMNBNNCFE-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 241001270131 Agaricus moelleri Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- IXLYQHHIFLEDCR-UHFFFAOYSA-N CC(C)(C=CC(C#N)=C1)C=C1C#N Chemical compound CC(C)(C=CC(C#N)=C1)C=C1C#N IXLYQHHIFLEDCR-UHFFFAOYSA-N 0.000 description 1
- NKMMDSVHGLNTEN-UHFFFAOYSA-N CC1C(C=CCC2)=C2SC1c1c(ccc2c(C3C=CC=CC3)cc(C3=Nc4ccccc4C3)c(cc3)c22)c2c3c(-c2ccccc2)c1 Chemical compound CC1C(C=CCC2)=C2SC1c1c(ccc2c(C3C=CC=CC3)cc(C3=Nc4ccccc4C3)c(cc3)c22)c2c3c(-c2ccccc2)c1 NKMMDSVHGLNTEN-UHFFFAOYSA-N 0.000 description 1
- OZURKAVFMUVNCM-UHFFFAOYSA-N CN(C)C1=C(C=CC=C1)N(C1=CC=CC=C1)F Chemical compound CN(C)C1=C(C=CC=C1)N(C1=CC=CC=C1)F OZURKAVFMUVNCM-UHFFFAOYSA-N 0.000 description 1
- LIELCGCMXLXDAB-UHFFFAOYSA-N Cc1ccc(C=N)c(-c2c(ccc(c3c(cc4)c(-c5nc(C)ccc5C#N)c5)c5-c5cc(-c6ccccc6)ccc5)c3c4c(-c3cccc(-c4ccccc4)c3)c2)n1 Chemical compound Cc1ccc(C=N)c(-c2c(ccc(c3c(cc4)c(-c5nc(C)ccc5C#N)c5)c5-c5cc(-c6ccccc6)ccc5)c3c4c(-c3cccc(-c4ccccc4)c3)c2)n1 LIELCGCMXLXDAB-UHFFFAOYSA-N 0.000 description 1
- QBDSZPLTLZSVIP-UHFFFAOYSA-N N#CC1=CCC(c2cc(-c3ccccc3)c(CC3)c4c2ccc(c(-c2ccccc2)c2)c4c3c2C(NC2)=CC=C2C#N)NC1 Chemical compound N#CC1=CCC(c2cc(-c3ccccc3)c(CC3)c4c2ccc(c(-c2ccccc2)c2)c4c3c2C(NC2)=CC=C2C#N)NC1 QBDSZPLTLZSVIP-UHFFFAOYSA-N 0.000 description 1
- XIGRROWPTHIRPH-UHFFFAOYSA-N N-[4-[4-[naphthalen-1-yl(pentyl)amino]phenyl]phenyl]-N-pentylnaphthalen-1-amine Chemical group C1(=CC=CC2=CC=CC=C12)N(CCCCC)C1=CC=C(C=C1)C1=CC=C(C=C1)N(C1=CC=CC2=CC=CC=C12)CCCCC XIGRROWPTHIRPH-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 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
- 239000003086 colorant Substances 0.000 description 1
- 238000000151 deposition 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
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- ABMYEXAYWZJVOV-UHFFFAOYSA-N pyridin-3-ylboronic acid Chemical compound OB(O)C1=CC=CN=C1 ABMYEXAYWZJVOV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/16—Electron 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
-
- 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
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
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- Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Electroluminescent Light Sources (AREA)
Abstract
Description
Claims (7)
- 제1항에 있어서,상기 치환되거나 치환되지 않은 A, B 는 각각 페닐(phenyl), 바이페닐(biphenyl), 파이리디닐(pyridyl), 나프틸(naphthyl), 퀴놀리닐(quinolinyl), 이소퀴놀리닐(isoquinolinyl), 플로레닐(fluorenyl), 터페닐(terphenyl), 메틸(methyl), 에틸(ethyl), 프로필(propyl), 이소프로필(i-propyl), 할로겐(halogen), 페난스롤리닐(phenanthrolinyl),퀴녹살리닐(quinoxalinyl), 터피리디닐(terpyridinyl) 및 이들의 치환체로부터 선택된 것을 특징으로 하는 전자 전달 화합물.
- 제2항에 있어서,상기 A, B가 치환된 경우, A, B의 치환기는 아릴(aryl), 알킬(alkyl), 아릴옥시(aryloxy), 알콕시(alkoxy), 알릴아미노(allylamino), 알킬아미노(alkylamino), 할로겐(halogen), 시아노(cyano)로 이루어진 군으로부터 선택된 것을 특징으로 하는 전자 전달 화합물.
- 제2항에 있어서,상기 A, B가 치환된 경우, A, B 의 치환기는 각각 독립적으로 페닐(phenyl), 바이페닐(biphenyl), 트리페닐메틸(triphenylmethyl), 페닐에틸리덴(phenylethylidene), 디페닐에틸리덴(diphenylethylidene), 페닐메틸리다인(phenylmethylidyne), 페녹시(phenoxy), 톨리옥시(tolyoxy), 메틸(methyl), 에틸(ethyl), 프로필(propyl), 이소프로필(iso-propyl), 터셔리부틸(t-butyl), 사이클로헥실(cyclohexyl), 디페닐아미노(diphenylamino), 모폴린(morpholine), 메톡시(methoxy), 에톡시(ethoxy), 프로폭시(propoxy), 부톡시(butoxy), 디메틸아미노(dimethylamino), 디페닐아미노(diphenylamino), 불소 및 염소로 이루어지는 군으로부터 선택된 것을 특징으로 하는 전자 전달 화합물.
- 제1항에 있어서,상기 전자 전달 화합물은 다음 화학식 3 중의 어느 하나인 것을 특징으로 하는 전자 전달 화합물.[화학식3]EA-1 EA-2 EA-3 EA-4EA-5 EA-6 EA-7 EA-8EA-9 EA-10 EA-11EA-12 EA-13 EA-14 EA-15EA-16 EA-17 EA-18 EA-19EA-20 EA-21 EA-22 EA-23EA-24 EA-25 EA-26 EA-27EA-28 EA-29 EA-30 EA-31EA-32 EA-33 EA-34 EA-35EA-36 EA-37 EA-38 EA-39EA-40 EA-41 EB-1 EB-2EB-3 EB-4 EB-5 EB-6EB-7 EB-8 EB-9 EB-10EB-11 EB-12 EC-1 EC-2EC-3 EC-4 EC-5 EC-6EC-7 EC-8 EC-9 EC-10EC-11 EC-12 ED-1 ED-2ED-3 ED-4 ED-5 ED-6ED-7 ED-8 ED-9 ED-10ED-11 ED-12 EE-1 EE-2EE-3 EE-4 EE-5EE-6 EE-7 EE-8EE-9 EE-10 EE-11EE-12 EF-1 EF-2EF-3 EF-4 EF-5EF-6 EF-7 EF-8EF-9 EF-10 EF-11EF-12 EG-1 EG-2EG-3 EG-4 EG-5EG-6 EG-7 EG-8 EG-9EG-10 EG-11 EG-12 EH-1EH-2 EH-3 EH-4 EH-5EH-6 EH-7 EH-8 EH-9EH-10 EH-11 EH-12 EI-1EI-2 EI-3 EI-4 EI-5EI-6 EI-7 EI-8 EI-9EI-10 EI-11 EI-12
- 제1항 내지 제6항의 전자 전달 화합물을 포함하는 전자전달층을 갖는 유기 전계 발광소자.
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KR1020050064458A KR100747313B1 (ko) | 2005-07-15 | 2005-07-15 | 전자 전달 화합물 및 이를 포함하는 유기전계발광소자 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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KR1020050064458A KR100747313B1 (ko) | 2005-07-15 | 2005-07-15 | 전자 전달 화합물 및 이를 포함하는 유기전계발광소자 |
Publications (2)
Publication Number | Publication Date |
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KR20070009304A true KR20070009304A (ko) | 2007-01-18 |
KR100747313B1 KR100747313B1 (ko) | 2007-08-07 |
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KR1020050064458A KR100747313B1 (ko) | 2005-07-15 | 2005-07-15 | 전자 전달 화합물 및 이를 포함하는 유기전계발광소자 |
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JP2004075567A (ja) * | 2002-08-12 | 2004-03-11 | Idemitsu Kosan Co Ltd | オリゴアリーレン誘導体及びそれを利用した有機エレクトロルミネッセンス素子 |
US6852429B1 (en) | 2003-08-06 | 2005-02-08 | Canon Kabushiki Kaisha | Organic electroluminescent device based on pyrene derivatives |
JP2005126431A (ja) | 2003-10-03 | 2005-05-19 | Semiconductor Energy Lab Co Ltd | ピレン誘導体、発光素子、および発光装置、並びに電気器具 |
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- 2005-07-15 KR KR1020050064458A patent/KR100747313B1/ko active IP Right Grant
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