KR20040069049A - 적색 발광물질 및 이를 포함하는 유기 전기발광 소자 - Google Patents
적색 발광물질 및 이를 포함하는 유기 전기발광 소자 Download PDFInfo
- Publication number
- KR20040069049A KR20040069049A KR1020030005470A KR20030005470A KR20040069049A KR 20040069049 A KR20040069049 A KR 20040069049A KR 1020030005470 A KR1020030005470 A KR 1020030005470A KR 20030005470 A KR20030005470 A KR 20030005470A KR 20040069049 A KR20040069049 A KR 20040069049A
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- South Korea
- Prior art keywords
- substituted
- formula
- unsubstituted
- substituent group
- phenyl
- Prior art date
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- 239000000463 material Substances 0.000 title claims abstract description 43
- 125000001424 substituent group Chemical group 0.000 claims abstract description 51
- -1 aminophenyl group Chemical group 0.000 claims abstract description 21
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 18
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000001624 naphthyl group Chemical group 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 10
- 150000002367 halogens Chemical class 0.000 claims abstract description 10
- 239000010410 layer Substances 0.000 claims description 84
- 150000001875 compounds Chemical class 0.000 claims description 36
- 239000012044 organic layer Substances 0.000 claims description 18
- 229910052739 hydrogen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 14
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 12
- 229910052751 metal Inorganic materials 0.000 claims description 11
- 239000002184 metal Substances 0.000 claims description 11
- 239000000758 substrate Substances 0.000 claims description 11
- 125000000623 heterocyclic group Chemical group 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 8
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 4
- 239000003377 acid catalyst Substances 0.000 claims description 4
- 150000008365 aromatic ketones Chemical class 0.000 claims description 4
- 238000006482 condensation reaction Methods 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- LFDDDMGBJBLSMD-ZZXKWVIFSA-N (e)-2-(dimethylamino)but-2-enedinitrile Chemical compound CN(C)C(\C#N)=C\C#N LFDDDMGBJBLSMD-ZZXKWVIFSA-N 0.000 claims description 2
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 claims description 2
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004986 diarylamino group Chemical group 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims description 2
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 2
- 229910052709 silver Inorganic materials 0.000 claims description 2
- 239000004332 silver Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 abstract description 13
- 239000000126 substance Substances 0.000 abstract description 9
- 229910052757 nitrogen Inorganic materials 0.000 abstract description 8
- 238000005401 electroluminescence Methods 0.000 abstract description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 2
- 125000005842 heteroatom Chemical group 0.000 abstract 2
- 229910052760 oxygen Inorganic materials 0.000 abstract 2
- 239000001301 oxygen Substances 0.000 abstract 2
- 229910052717 sulfur Inorganic materials 0.000 abstract 2
- 125000004434 sulfur atom Chemical group 0.000 abstract 2
- 125000005605 benzo group Chemical group 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 18
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 230000005525 hole transport Effects 0.000 description 11
- 238000002347 injection Methods 0.000 description 7
- 239000007924 injection Substances 0.000 description 7
- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 230000018044 dehydration Effects 0.000 description 4
- 238000006297 dehydration reaction Methods 0.000 description 4
- DPZSNGJNFHWQDC-ARJAWSKDSA-N (z)-2,3-diaminobut-2-enedinitrile Chemical compound N#CC(/N)=C(/N)C#N DPZSNGJNFHWQDC-ARJAWSKDSA-N 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 239000010408 film Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 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 3
- 230000006872 improvement Effects 0.000 description 3
- 238000005424 photoluminescence Methods 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 239000012265 solid product Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 2
- 239000000956 alloy Substances 0.000 description 2
- 229910045601 alloy Inorganic materials 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000005281 excited state Effects 0.000 description 2
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound 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
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- GMMYHFWPAAFOKN-UHFFFAOYSA-N 1,1'-biphenyl;n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1C1=CC=CC=C1.C=1C=CC2=CC=CC=C2C=1NC1=CC=CC=C1 GMMYHFWPAAFOKN-UHFFFAOYSA-N 0.000 description 1
- PJQMYUHLAJJKJK-UHFFFAOYSA-N 2-[3-[2-[4-(dimethylamino)phenyl]ethenyl]-5,5-dimethylcyclohex-2-en-1-ylidene]propanedinitrile Chemical compound C1=CC(N(C)C)=CC=C1C=CC1=CC(=C(C#N)C#N)CC(C)(C)C1 PJQMYUHLAJJKJK-UHFFFAOYSA-N 0.000 description 1
- BGNGWHSBYQYVRX-UHFFFAOYSA-N 4-(dimethylamino)benzaldehyde Chemical compound CN(C)C1=CC=C(C=O)C=C1 BGNGWHSBYQYVRX-UHFFFAOYSA-N 0.000 description 1
- UESSERYYFWCTBU-UHFFFAOYSA-N 4-(n-phenylanilino)benzaldehyde Chemical compound C1=CC(C=O)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UESSERYYFWCTBU-UHFFFAOYSA-N 0.000 description 1
- BTEAMLUWLVUBFF-UHFFFAOYSA-N 5-(3-methylphenyl)-4-phenylcyclohexa-2,4-diene-1,1-diamine Chemical compound CC=1C=C(C=CC1)C1=C(C=CC(C1)(N)N)C1=CC=CC=C1 BTEAMLUWLVUBFF-UHFFFAOYSA-N 0.000 description 1
- CFNMUZCFSDMZPQ-GHXNOFRVSA-N 7-[(z)-3-methyl-4-(4-methyl-5-oxo-2h-furan-2-yl)but-2-enoxy]chromen-2-one Chemical compound C=1C=C2C=CC(=O)OC2=CC=1OC/C=C(/C)CC1OC(=O)C(C)=C1 CFNMUZCFSDMZPQ-GHXNOFRVSA-N 0.000 description 1
- 229910052693 Europium Inorganic materials 0.000 description 1
- 229910006404 SnO 2 Inorganic materials 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 239000007772 electrode material Substances 0.000 description 1
- OGPBJKLSAFTDLK-UHFFFAOYSA-N europium atom Chemical compound [Eu] OGPBJKLSAFTDLK-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- WJWKNRDTZSGMCE-UHFFFAOYSA-N indium;oxolead Chemical compound [In].[Pb]=O WJWKNRDTZSGMCE-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- NMVZHJHQIMLNBM-UHFFFAOYSA-N n,n-dimethyl-4-[2-(6-methyl-4h-pyran-2-yl)ethenyl]aniline Chemical compound C1=CC(N(C)C)=CC=C1C=CC1=CCC=C(C)O1 NMVZHJHQIMLNBM-UHFFFAOYSA-N 0.000 description 1
- DCZNSJVFOQPSRV-UHFFFAOYSA-N n,n-diphenyl-4-[4-(n-phenylanilino)phenyl]aniline Chemical class C1=CC=CC=C1N(C=1C=CC(=CC=1)C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC=CC=1)C1=CC=CC=C1 DCZNSJVFOQPSRV-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000002524 organometallic group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- 238000000103 photoluminescence spectrum Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 125000004309 pyranyl group Chemical group O1C(C=CC=C1)* 0.000 description 1
- 238000005215 recombination Methods 0.000 description 1
- 230000006798 recombination Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000003786 synthesis reaction 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
- 125000005580 triphenylene group Chemical group 0.000 description 1
- 229910021642 ultra pure water Inorganic materials 0.000 description 1
- 239000012498 ultrapure water Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
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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
-
- 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]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
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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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1007—Non-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
- C09K2211/1003—Carbocyclic compounds
- C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
-
- 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
-
- 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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- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Organic Chemistry (AREA)
- Optics & Photonics (AREA)
- Electroluminescent Light Sources (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Description
Claims (7)
- 하기 화학식 1로 표시되는 적색 발광물질:화학식 1상기 식에서,R1, R2, R3, R4, R5및 R6는 각각 독립적으로 수소; 비치환되거나 치환된 C1-C10알킬; 비치환되거나 치환된 C1-C10알콕시; 비치환되거나 치환된 C1-C10알킬옥시; 또는 비치환되거나 치환된 페닐이고, 이때 치환기는 알킬, 할로겐, 알콕시, 알킬옥시, 하이드록시, 페닐 또는 나프틸이고, R1, R3및 R4, 또는 R2, R5및 R6는 서로 동종환 또는 이종환을 형성할 수 있고;R7, R8및 R9은 각각 독립적으로 비치환되거나 메틸기로 1 내지 4개 치환된 벤조 5원 복소환 또는 벤조 6원 복소환; 비치환되거나 치환기군 a 중에서 선택되는 1종 이상의 치환기로 1 내지 4개 치환된 페닐, 나프틸, 5원 복소환 또는 6원 복소환; 또는하기 화학식 2로 표시되는 아미노 페닐:화학식 2(여기서, A1, A3, A5및 A6는 각각 독립적으로 수소, 또는 치환기군 a 중에서 선택되는 기이고;A2또는 A4는 각각 독립적으로 수소, R13또는 R14이고, 여기서 A1과 A2, 또는 A3와 A4는 서로 이종환을 형성할 수 있음)이고;이때, 상기 치환기군 a는중에서 선택되고,여기에서, R10은 수소 또는 C1-C10알킬이고,R11 또는 R12는 C1-C10알킬렌, 바람직하게는 메틸렌, 에틸렌, 프로필렌, 부틸렌, sec-부틸렌, tert-부틸렌, 펜틸렌, 2-페닐이소프로필렌 또는 트리클로로메틸렌이고,R13은 비치환되거나, 치환기군 b 또는 치환기군 c 중에서 선택되는 1종 이상의 치환기로 1 내지 2개 치환된 페닐; 또는 비치환되거나, 치환기군 c 중에서 선택되는 1종 이상의 치환기로 1 내지 4개 치환된 나프틸이고,R14은 비치환되거나, 치환기군 c 중에서 선택되는 1종 이상의 치환기로 1 내지 2개 치환된 페닐; 또는 비치환되거나, 치환기군 c 중에서 선택되는 1종 이상의 치환기로 1 내지 4개 치환된 나프틸이고,R15은 C1-C10알킬; 또는 비치환되거나, 치환기군 c 중에서 선택되는 1종 이상의 치환기로 1 내지 2개 치환된 페닐이고,R16은 할로겐; C1-C10알콕시; 또는 비치환되거나, 치환기군 c 중에서 선택되는 1종 이상의 치환기로 1 내지 2개 치환된 페닐이고,R17은 C5-C10시클로알킬; C1-C10알킬; 2-하이드록시에틸; 또는 비치환되거나, 치환기군 c 중에서 선택되는 1종 이상의 치환기로 1 내지 2개 치환된 페닐이고,여기에서, 치환기군 b는이고,치환기군 c는이고,여기에서, R18은 수소 또는 C1-C10알킬이고,R19 및 R21은 C1-C10알킬렌이고,R20는 할로겐이고,R22는 C1-C10알킬; 또는 비치환되거나, 상기 치환기군 c 중에서 선택되는 1종 이상의 치환기로 1 내지 2개 치환된 페닐이고,R23및 R24는 각각 독립적으로 수소 또는 C1-C4알킬이다.
- 제 1 항에 있어서,R1, R2, R3, R4, R5및 R6는 각각 수소; C1-C6알킬; 또는 비치환되거나 알킬, 할로겐, 알콕시, 알킬옥시, 하이드록시, 페닐 또는 나프틸로 치환된 페닐이고, R1, R3및 R4, 또는 R2, R5및 R6는 서로 동종환 또는 이종환을 형성할 수 있고;R7, R8및 R9은 디알킬아미노 또는 디아릴아미노로 치환된 아미노 페닐이고, 치환기는 서로 동종환 또는 이종환을 형성할 수 있는 적색 발광물질.
- 하기 화학식 3의 디메틸아미노말레오니트릴, 하기 화학식 4의 아로마틱 케톤 또는 알데히드 화합물, 및 화학식 5 또는 하기 화학식 6의 아로마틱 케톤 또는 알데히드 화합물을 산 촉매 존재 하에서 축합반응시키는 것을 포함하는, 제 1 항에 따른 화학식 1의 화합물의 제조방법:화학식 3화학식 4화학식 5화학식 6상기 식에서, R1, R2, R3, R4, R5및 R6는 제 1 항에서 정의한 바와 같다.
- 제 3 항에 있어서,화학식 4, 화학식 5 및 화학식 6의 화합물은 화학식 3의 화합물에 대하여 각각 1 내지 2 당량 사용하는 것을 특징으로 하는 방법.
- 제 3 항에 있어서,축합반응을 70 내지 120 ℃에서 1 내지 72 시간 동안 수행하는 것을 특징으로 하는 방법.
- 기판, 투명전극, 유기층 및 금속전극이 순차적으로 적층된 유기 전기발광 소자에 있어서, 유기층에 제 1 항에 따른 화학식 1의 화합물을 발광물질로서 포함하는 것을 특징으로 하는 유기 전기발광 소자.
- 제 6 항에 있어서,유기층이, 전자 수송층/발광층/정공 수송층, 전자 수송성 발광층/정공 수송층, 또는 전자 수송층/정공 수송성 발광층으로 구성된 것임을 특징으로 하는 유기 전기발광 소자.
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