KR19990078127A - Organic Electroluminescence Material and Device Using the Same - Google Patents
Organic Electroluminescence Material and Device Using the Same Download PDFInfo
- Publication number
- KR19990078127A KR19990078127A KR1019990009762A KR19990009762A KR19990078127A KR 19990078127 A KR19990078127 A KR 19990078127A KR 1019990009762 A KR1019990009762 A KR 1019990009762A KR 19990009762 A KR19990009762 A KR 19990009762A KR 19990078127 A KR19990078127 A KR 19990078127A
- Authority
- KR
- South Korea
- Prior art keywords
- organic electroluminescent
- light emitting
- electroluminescent device
- group
- layer
- Prior art date
Links
- 239000000463 material Substances 0.000 title claims abstract description 84
- 238000005401 electroluminescence Methods 0.000 title claims 3
- SJHPCNCNNSSLPL-CSKARUKUSA-N (4e)-4-(ethoxymethylidene)-2-phenyl-1,3-oxazol-5-one Chemical class O1C(=O)C(=C/OCC)\N=C1C1=CC=CC=C1 SJHPCNCNNSSLPL-CSKARUKUSA-N 0.000 claims abstract description 20
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
- 125000003277 amino group Chemical group 0.000 claims abstract description 3
- 125000006615 aromatic heterocyclic group Chemical group 0.000 claims abstract description 3
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 claims abstract description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 3
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
- 238000006467 substitution reaction Methods 0.000 claims abstract description 3
- 239000010410 layer Substances 0.000 claims description 129
- -1 quinoline metal complex Chemical class 0.000 claims description 59
- 239000000758 substrate Substances 0.000 claims description 28
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 claims description 11
- 239000002346 layers by function Substances 0.000 claims description 11
- 239000000126 substance Substances 0.000 claims description 6
- 238000001228 spectrum Methods 0.000 claims 2
- 239000000470 constituent Substances 0.000 abstract 1
- 239000010408 film Substances 0.000 description 28
- 238000000034 method Methods 0.000 description 23
- 238000000151 deposition Methods 0.000 description 19
- 230000005525 hole transport Effects 0.000 description 18
- 230000008021 deposition Effects 0.000 description 17
- 229910052757 nitrogen Inorganic materials 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 11
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000011521 glass Substances 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000001257 hydrogen Substances 0.000 description 7
- 239000010409 thin film Substances 0.000 description 7
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 6
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 6
- 230000005611 electricity Effects 0.000 description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- 229910002804 graphite Inorganic materials 0.000 description 5
- 239000010439 graphite Substances 0.000 description 5
- 150000002431 hydrogen Chemical group 0.000 description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 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 description 4
- 238000002347 injection Methods 0.000 description 4
- 239000007924 injection Substances 0.000 description 4
- 238000006862 quantum yield reaction Methods 0.000 description 4
- 238000001771 vacuum deposition Methods 0.000 description 4
- MWMNLUGPPZOPJQ-UHFFFAOYSA-N 4-(4-aminophenyl)-3-naphthalen-1-ylaniline Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1C1=CC=CC2=CC=CC=C12 MWMNLUGPPZOPJQ-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 3
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000002019 doping agent Substances 0.000 description 3
- 230000001747 exhibiting effect Effects 0.000 description 3
- 239000011737 fluorine Substances 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 229910052744 lithium Inorganic materials 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012044 organic layer Substances 0.000 description 3
- 238000004528 spin coating Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 238000007740 vapor deposition Methods 0.000 description 3
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 2
- 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 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 241000284156 Clerodendrum quadriloculare Species 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 2
- 125000004423 acyloxy group Chemical group 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 150000004696 coordination complex Chemical class 0.000 description 2
- 150000004775 coumarins Chemical class 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229910052738 indium Inorganic materials 0.000 description 2
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 229910052749 magnesium Inorganic materials 0.000 description 2
- 239000011777 magnesium Substances 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000011368 organic material Substances 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- CRGSMSNUTNRNQM-UHFFFAOYSA-N 2-(4-tert-butylphenyl)-1,3,4-oxadiazole Chemical compound C1=CC(C(C)(C)C)=CC=C1C1=NN=CO1 CRGSMSNUTNRNQM-UHFFFAOYSA-N 0.000 description 1
- QKCKCXFWENOGER-UHFFFAOYSA-N 2-phenyloxazol-5(4H)-one Chemical compound O1C(=O)CN=C1C1=CC=CC=C1 QKCKCXFWENOGER-UHFFFAOYSA-N 0.000 description 1
- CMSGUKVDXXTJDQ-UHFFFAOYSA-N 4-(2-naphthalen-1-ylethylamino)-4-oxobutanoic acid Chemical compound C1=CC=C2C(CCNC(=O)CCC(=O)O)=CC=CC2=C1 CMSGUKVDXXTJDQ-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
- 229910001316 Ag alloy Inorganic materials 0.000 description 1
- 229910000838 Al alloy Inorganic materials 0.000 description 1
- 229910001148 Al-Li alloy Inorganic materials 0.000 description 1
- 229910017073 AlLi Inorganic materials 0.000 description 1
- 241000272525 Anas platyrhynchos Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- GYHNNYVSQQEPJS-UHFFFAOYSA-N Gallium Chemical compound [Ga] GYHNNYVSQQEPJS-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910000846 In alloy Inorganic materials 0.000 description 1
- CBENFWSGALASAD-UHFFFAOYSA-N Ozone Chemical compound [O-][O+]=O CBENFWSGALASAD-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- JFBZPFYRPYOZCQ-UHFFFAOYSA-N [Li].[Al] Chemical compound [Li].[Al] JFBZPFYRPYOZCQ-UHFFFAOYSA-N 0.000 description 1
- JHYLKGDXMUDNEO-UHFFFAOYSA-N [Mg].[In] Chemical compound [Mg].[In] JHYLKGDXMUDNEO-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- SNAAJJQQZSMGQD-UHFFFAOYSA-N aluminum magnesium Chemical compound [Mg].[Al] SNAAJJQQZSMGQD-UHFFFAOYSA-N 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000001194 electroluminescence spectrum Methods 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- RBBOWEDMXHTEPA-UHFFFAOYSA-N hexane;toluene Chemical compound CCCCCC.CC1=CC=CC=C1 RBBOWEDMXHTEPA-UHFFFAOYSA-N 0.000 description 1
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
- 239000001989 lithium alloy Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000007773 negative electrode material Substances 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- AHLBNYSZXLDEJQ-FWEHEUNISA-N orlistat Chemical compound CCCCCCCCCCC[C@H](OC(=O)[C@H](CC(C)C)NC=O)C[C@@H]1OC(=O)[C@H]1CCCCCC AHLBNYSZXLDEJQ-FWEHEUNISA-N 0.000 description 1
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 1
- 150000004866 oxadiazoles Chemical class 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 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 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 238000004904 shortening Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000004544 sputter deposition Methods 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 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
- 150000003852 triazoles Chemical class 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
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000013585 weight reducing agent Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 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]
- H10K50/11—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
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—Carrier transporting layers
- H10K50/15—Hole transporting layers
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/14—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
- C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
-
- 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
Abstract
본 발명은 고휘도(高輝度)이며 긴 수명의 적색 발광 유기 전기발광(EL) 소자를 제공할 수가 있도록 하는 것이다.The present invention provides a high luminance and long lifetime red light emitting organic electroluminescent (EL) device.
유기 EL 소자의 발광층의 구성 소자로서 화학식 1로 표시되는 옥사졸론 유도체와 통상의 발광 재료를 혼합하여 사용한다.As an constituent element of the light emitting layer of the organic EL device, an oxazolone derivative represented by the formula (1) and a common light emitting material are mixed and used.
식중, R1및 R2는 각각 독립적으로 수소 원자, 할로겐기, 히드록실기, 치환 또는 비치환된 아미노기, 니트로기, 시아노기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 시클로알킬기, 치환 또는 비치환된 알콕시기, 치환 또는 비치환된 방향족 탄화수소기, 치환 또는 비치환된 방향족 복소환기, 치환 또는 비치환된 아르알킬기, 치환 또는 비치환된 아릴옥시기, 치환 또는 비치환된 알콕시카르보닐기 또는 카르복실기를 나타낸다.Wherein R 1 and R 2 are each independently a hydrogen atom, a halogen group, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substitution Or an unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, A substituted or unsubstituted alkoxycarbonyl group or carboxyl group is shown.
Description
본 발명은 유기 전기발광 소자 재료 및 그것을 사용한 유기 전기발광 소자에 관한 것이며, 예를 들면 평면 광원 또는 표시소자에 사용하기에 적합한 유기 전기발광 소자 재료 및 그것을 사용한 유기 전기발광 소자에 관한 것이다.The present invention relates to an organic electroluminescent device material and an organic electroluminescent device using the same, for example, to an organic electroluminescent device material suitable for use in a planar light source or a display device and an organic electroluminescent device using the same.
유기 전기발광 소자는 양극에서 주입된 정공과 음극에서 주입된 전자가 형광 능력을 갖는 발광층내에서 재결합하여 여기 상태에서 실활할 때에 광을 방사하는 현상을 이용하는 것이다. 이러한 연구는 유기 화합물의 높은 형광 양자 수율과 다종 다양하게 설계 가능한 분자 구조에 착안한 것이 시초였으나, 그 발광 휘도, 발광 효율은 낮아 실용 수준이라고는 할 수 없었다.The organic electroluminescent device utilizes a phenomenon of emitting light when the holes injected from the anode and the electrons injected from the cathode recombine in a light emitting layer having fluorescence capability and deactivate in an excited state. This research was focused on high fluorescence quantum yield of organic compounds and various molecular structures that can be designed in various ways.
그러나, 그 후 탱(Tang)과 밴스라이크(Vanslyke) 등은 발광층만의 구성으로, 정공을 수송하는 능력이 우수한 재료(이하, 정공 수송층이라 함)를 조합한 적층 구조를 취하는 것으로 각별히 그 성능이 향상된다는 것을 보고하였다(어플라이드 피직스 레터(Applied Physics Letter), 51권, 913페이지, 1987년). 이것을 계기로 연구는 정공을 주입하기만을 위한 역할을 갖는 층(정공 주입층), 전자를 수송하기만 하는 역할을 갖는 층(전자 수송층)등, 완전히 기능을 분리한다는 수법을 기본으로 한 것에 집중되어 각 유기 재료의 고성능화도와 더불어 표시 장치로서의 실용화가 가까워지고 있다. 이하에서는 발광층, 잔자 수송층, 정공 수송층, 및 정공 주입층을 총괄하여 유기 기능층이라 한다.However, since then, Tang and Vanslyke have only a light emitting layer, and have a laminated structure combining materials having excellent hole transport ability (hereinafter, referred to as a hole transport layer). Reported improvement (Applied Physics Letter, Vol. 51, p. 913, 1987). Based on this, the research focused on the method of completely separating the functions, such as a layer having only a role of injecting holes (hole injection layer) and a layer having only a role of transporting electrons (electron transport layer). In addition to high performance of each organic material, practical use as a display device is nearing. Hereinafter, the light emitting layer, the residue transport layer, the hole transport layer, and the hole injection layer are collectively referred to as an organic functional layer.
최근에는 녹색 발광계로서는 정공 주입층에 스타 버스트계 아민을 사용함으로써 휘도 10만 cd/㎡ 이상, 발광 휘도 101 m/W 이상(월간 디스플레이, 1995년 9월호), 연속 구동시의 휘도의 반감 수명 1만 시간 이상이 보고되었다. 또한, 청색 발광을 나타내는 유기 전기발광 소자로서는 디스티릴아릴렌 유도체를 발광 재료로 사용하여 2만 cd/㎡ 이상, 발광 휘도 51 m/W, 반감 수명 5천 시간 이상이 보고되었다(일본 화학회 제70춘계년회 특별 강연).In recent years, the use of a star burst type amine in the hole injection layer as a green light emitting system has a brightness of 100,000 cd / m 2 or more, a luminance of light of 101 m / W or more (monthly display, September 1995), and a half-life of luminance at continuous driving. More than 10,000 hours have been reported. In addition, as an organic electroluminescent device exhibiting blue light emission, at least 20,000 cd / m 2, emission luminance of 51 m / W, and half-life of more than 5,000 hours have been reported by using a distyryl arylene derivative as a light emitting material. 70th Spring Conference Special Lecture).
한편, 적색 발광을 나타내는 재료에 관해서는 원래 유기 화합물이 무기 반도체 재료보다도 넓은 밴드 갭을 갖는다는 특징을 갖기 때문에 분자 설계가 용이하지 않다는 것, 그리고 합성된 물질의 성막성이 곤란하거나 고순도화를 위한 정제 수율이 나쁘다는 등의 문제가 발생하는 이유에서 실용 수준으로까지는 이르지 못하고 있다.On the other hand, as for the material exhibiting red luminescence, since the original organic compound has a characteristic of having a wider band gap than the inorganic semiconductor material, the molecular design is not easy and the film forming property of the synthesized material is difficult or high purity. Problems such as poor tablet yield have not been reached to the practical level.
이러한 배경 속에서, 적색 발광 내지 다색화를 도모하는 방법으로서 특개평 3-152897에 개시된 바와 같은 시도가 이루어지고 있다. 이것은 유기 EL 소자의 전면에 색변환층이 있는 필터를 삽입하는 것이다. 이 필터는 유기 EL 소자로부터의 발광 파장에서 흡수함과 동시에 형광을 발한다는 특성을 갖는 것이다. 따라서, EL 소자로부터의 발광의 일부가 필터를 투과할 때에 색변환되어, 적색 내지 다색 발광으로서 나타나게 된다.In this background, attempts have been made as disclosed in Japanese Patent Laid-Open No. Hei 3-152897 as a method for achieving red light emission or multicoloring. This inserts a filter having a color conversion layer in front of the organic EL element. This filter has a characteristic of absorbing at the emission wavelength from the organic EL element and emitting fluorescence. Therefore, a part of the light emission from the EL element is color converted when passing through the filter, and appears as red to multicolor light emission.
그러나, 이 방법으로는, EL 발광을 필터로 색변환하기 위한 양자 수율에 한계가 있기 때문에 충분한 발광 효율을 얻을 수 없다는 것과, 필터 사용에 의한 고비용을 피할 수가 없다는 문제가 있었다. 한편, 적색 발광을 나타내는 EL 재료를 개시한 예로서 특개평 7-288184에 개시된 바와 같은 프탈로시아닌계 화합물을 들 수 있다.However, this method has a problem in that sufficient light emission efficiency cannot be obtained because there is a limit in the quantum yield for color conversion of EL light emission into a filter, and that high cost by use of a filter cannot be avoided. On the other hand, examples of the disclosure of EL materials exhibiting red light emission include phthalocyanine compounds as disclosed in Japanese Patent Laid-Open No. Hei 7-288184.
식중, X는 수소이고, M은 마그네슘, 리튬, 나트륨, 칼슘, 아연, 알루미늄, 갈륨 및 인듐으로 이루어지는 군으로부터 선택되며(Y), B는 B가 0 또는 1이며, B가 1인 경우에 Y는 염소 및 불소로 이루어지는 군으로부터 선택된다.Wherein X is hydrogen, M is selected from the group consisting of magnesium, lithium, sodium, calcium, zinc, aluminum, gallium and indium (Y), B is Y when B is 0 or 1 and B is 1 Is selected from the group consisting of chlorine and fluorine.
특개평 7-166159호에 개시되어 있는 4-히드록시아크리딘 화합물,4-hydroxyacridine compound disclosed in Japanese Patent Laid-Open No. 7-166159,
식중, M은 주기율표의 2족, 3족의 금속이다.In the formula, M is a metal of group 2 and 3 of the periodic table.
특개평 7-90259에 개시된 바와 같은 비오라이트류 화합물, 및Biolite compounds as disclosed in Japanese Patent Laid-Open No. 7-90259, and
식중, R1, R2, R3, R4, R5및 R6은 동일 또는 상이하며, 수소 원자, 할로겐 원자, 저급 알킬기, 저급 알콕시기, 페닐기, 디알틸아미노기, 디페닐아미노기를 나타낸다.In formula, R <1> , R <2> , R <3> , R <4> , R <5> and R <6> are the same or different, and represent a hydrogen atom, a halogen atom, a lower alkyl group, a lower alkoxy group, a phenyl group, a dialtylamino group, and a diphenylamino group.
특개평 7-238280에 개시되어 비오란트론 유도체 등을 들 수 있다.It is disclosed in Unexamined-Japanese-Patent No. 7-238280, etc. are mentioned.
식중, R은 H,CnH2n+1,CnH2n+10,NH2,N(C6H5)2,NO2,CF3또는 할로겐 원자로 이루어지는 군으로부터 선택된다.Wherein R is selected from the group consisting of H, C n H 2n + 1 , C n H 2n + 10 , NH 2 , N (C 6 H 5 ) 2 , NO 2 , CF 3 or a halogen atom.
이러한 재료를 사용한 적색 발광 소자의 구조를 도 6을 기초로 설명한다. 우선, 투명 절연성 지지 기판(201) 위에 양극으로서 투명 도전성 박막(202)을 적층한다. 다시 그 상부에 정공 수송층(203), 상기 적색 발광층(204), 전자 수송층(204)을 적층하고 마지막으로 상부 음극층(206)을 성막한다.The structure of the red light emitting element using this material will be described based on FIG. First, the transparent conductive thin film 202 is laminated as an anode on the transparent insulating support substrate 201. The hole transport layer 203, the red light emitting layer 204, and the electron transport layer 204 are stacked on top of each other, and finally, the upper cathode layer 206 is formed.
적색 발광층(204)은 정공 및 전자의 주입, 수송 능력이 낮기 때문에, 정공 수송층(203)과 전자 수송층(205)으로 협지함으로써 고효율화를 도모할 수가 있다. 그러나, 상기 적색 발광 재료는 형광의 양자 수율이 낮아 소자 내부에 흐르는 전류량을 증가시켜도 약 1000 cd/㎡ 정도의 휘도로 밖에 발광되지 않아 실용성에는 부족한 것이었다. 또한, 천연색 표시를 위한 청색 내지 백색 발광을 위한 기술로서 쿠마린 유도체를 사용한 예로서는 특개평 8-157815에 개시된 쿠마린 유도체와 특정 구조 화합물과의 혼합 재료를 들 수가 있다.Since the red light emitting layer 204 has low hole and electron injection and transporting ability, the red light emitting layer 204 is sandwiched between the hole transporting layer 203 and the electron transporting layer 205 to achieve high efficiency. However, the red light-emitting material has a low quantum yield of fluorescence, and thus only emits light with a luminance of about 1000 cd / m 2 even if the amount of current flowing inside the device is increased, which is insufficient in practicality. Further, examples of using coumarin derivatives as a technique for blue to white light emission for natural color display include a mixed material of coumarin derivatives disclosed in Japanese Patent Application Laid-open No. Hei 8-157815 and specific structural compounds.
식중, R1내지 R5는 독립적으로 수소, 불소, 알킬기, 알콕시기, 디알킬아미노기, 알카노일옥시기, 알킬옥시카르보닐기, 아릴기, 시아노기, 아카노일기 또는 트리플루오로메틸기로부터 선택되며, x는 O 또는 NY(Y는 수소, 알킬기 또는 아릴기를 나타낸다)를 나타내며, n은 0, 1 또는 2를 나타내며, R6은 수소 또는 메틸기를 나타낸다.Wherein R 1 to R 5 are independently selected from hydrogen, fluorine, alkyl group, alkoxy group, dialkylamino group, alkanoyloxy group, alkyloxycarbonyl group, aryl group, cyano group, akanoyl group or trifluoromethyl group, x represents O or NY (Y represents hydrogen, an alkyl group or an aryl group), n represents 0, 1 or 2, and R <6> represents hydrogen or a methyl group.
특개평 7-126330, 특개평 7-188340에 개시된 쿠마린 유도체와 특정 구조를 갖는 화합물과의 혼합 재료를 들 수가 있다.The mixed material of the coumarin derivative disclosed in Unexamined-Japanese-Patent No. 7-126330 and Unexamined-Japanese-Patent No. 7-188340, and the compound which has a specific structure is mentioned.
식중, R1내지 R5는 독립적으로 수소, 불소, 알킬기, 알콕시기, 디알킬아미노기, 알카노일옥시기, 알킬옥시카르보닐기, 아릴기, 시아노기, 아카노일기 또는 트리플루오로메틸기로부터 선택되며, x는 O 또는 NY(Y는 수소, 알킬기 또는 아릴기를 나타낸다)를 나타내며, n은 0, 1 또는 2를 나타내며, R6은 수소 또는 메틸기를 나타낸다.Wherein R 1 to R 5 are independently selected from hydrogen, fluorine, alkyl group, alkoxy group, dialkylamino group, alkanoyloxy group, alkyloxycarbonyl group, aryl group, cyano group, akanoyl group or trifluoromethyl group, x represents O or NY (Y represents hydrogen, an alkyl group or an aryl group), n represents 0, 1 or 2, and R <6> represents hydrogen or a methyl group.
이러한 유기 재료를 발광층으로서 사용했을 경우, 안정한 청색 발광이 얻어지며, 또한, 발광층에 대하여 녹색계, 적색계의 도판트 재료를 혼입함으로써 백색 발광이 가능해진다. 그러나 어떤 적색 발광 재료를 사용하여도 충분한 휘도가 얻어지지 않아 다색화를 시도했을 경우, 색 균형 저하의 원인이 된다.When such an organic material is used as the light emitting layer, stable blue light emission is obtained, and white light emission is possible by mixing green and red dopant materials in the light emitting layer. However, sufficient luminance is not obtained by using any red light-emitting material, and multicolorization is attempted, which causes color balance deterioration.
두번째 문제는, 성막성의 문제를 들 수 있다. 상기 쿠마린 유도체는 분자량 50만 장도의 고분자이기 때문에, 통상의 성막법인 저항 가열형의 진공 증착이 이루어지지 않아 톨루엔, 아세톤 등의 유기 용제에 용해시키는 스핀코팅법을 취하지 않을 수 없다. 회전수 6000 rpm 정도로 코팅했을 경우, 성막의 균일성이 진공 증착법과 비교하여 수% 내지 수십%가 떨어질 뿐만 아니라, 막중에 수미크론 단위에서 결함이 발생할 우려가 있으며, 나아가 유기 EL 소자의 수명을 단축하는 요인으로도 될 수 있다.The second problem is a problem of film formation. Since the coumarin derivative is a polymer having a molecular weight of 500,000 sheets, a spin coating method for dissolving in an organic solvent such as toluene, acetone, etc. cannot be performed because a vacuum deposition of a resistive heating type, which is a conventional film forming method, is not performed. When coated at a rotational speed of about 6000 rpm, the uniformity of the film formation is not only lowered by several to several tens of percent compared to the vacuum deposition method, but defects may occur in several micron units in the film, further shortening the life of the organic EL element. It can also be a factor.
도 1은 본 발명에 따른 전기발광(EL) 소자의 단면도.1 is a cross-sectional view of an electroluminescent (EL) device according to the invention.
도 2는 본 발명에 따른 EL 소자의 단면도.2 is a cross-sectional view of an EL element according to the present invention.
도 3은 본 발명에 관한 EL 소자의 단면도.3 is a cross-sectional view of an EL element according to the present invention.
도 4는 본 발명에 따른 EL 소자의 단면도.4 is a cross-sectional view of an EL element according to the present invention.
도 5는 본 발명에 따른 EL 소자의 단면도.5 is a sectional view of an EL element according to the present invention;
도 6은 종래의 유기 EL 소자의 일례를 나타내는 사시도.6 is a perspective view illustrating an example of a conventional organic EL device.
<도면의 주요 부분에 대한 부호의 설명><Explanation of symbols for the main parts of the drawings>
1 유리 기판1 glass substrate
2 양극2 anode
3 음극3 cathode
4 발광층4 light emitting layer
5 정공 수송층5 hole transport layer
6 전자 수송층6 electron transport layer
201 투명 지지 기판201 transparent support substrate
202 투명 도전성 박막202 Transparent Conductive Thin Film
203 정공 수송층203 hole transport layer
204 적색 발광층204 red light emitting layer
205 전자 수송층205 electron transport layer
206 상부 음극층206 Top Cathode Layer
청구범위에 기재된 유기 전기발광 소자 재료는 하기 화학식 1로 표시되는 옥사졸론 유도체로 이루어지는 것을 특징으로 한다.The organic electroluminescent device material described in the claims is characterized by consisting of an oxazolone derivative represented by the following formula (1).
<화학식 1><Formula 1>
식중, R1및 R2는 각각 독립적으로 수소 원자, 할로겐기, 히드록실기, 치환 또는 비치환된 아미노기, 니트로기, 시아노기, 치환 또는 비치환된 알킬기, 치환 또는 비치환된 알케닐기, 치환 또는 비치환된 시클로알킬기, 치환 또는 비치환된 알콕시기, 치환 또는 비치환된 방향족 탄화수소기, 치환 또는 비치환된 방향족 복소환기, 치환 또는 비치환된 아르알킬기, 치환 또는 비치환된 아릴옥시기, 치환 또는 비치환된 알콕시카르보닐기 또는 카르복실기를 나타낸다.Wherein R 1 and R 2 are each independently a hydrogen atom, a halogen group, a hydroxyl group, a substituted or unsubstituted amino group, a nitro group, a cyano group, a substituted or unsubstituted alkyl group, a substituted or unsubstituted alkenyl group, a substitution Or an unsubstituted cycloalkyl group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted aromatic hydrocarbon group, a substituted or unsubstituted aromatic heterocyclic group, a substituted or unsubstituted aralkyl group, a substituted or unsubstituted aryloxy group, A substituted or unsubstituted alkoxycarbonyl group or carboxyl group is shown.
청구항 2에 기재한 유기 전기발광 소자는, 한쌍의 전극간에 1층 이상의 발광층을 포함하는 유기 기능층을 협지한 유기 전기발광 소자에 있어서, 상기 유기 기능층의 1층을 구성하는 재료가 상기 하기 화학식 1로 표시되는 옥사졸론 유도체로 이루어지는 유기 전기발광 소자 재료를 함유하는 것을 특징으로 한다.The organic electroluminescent device according to claim 2 is an organic electroluminescent device in which an organic functional layer including one or more light emitting layers is sandwiched between a pair of electrodes, wherein a material constituting one layer of the organic functional layer is represented by the following chemical formula: It is characterized by containing the organic electroluminescent element material which consists of an oxazolone derivative represented by 1. It is characterized by the above-mentioned.
청구항 3에 기재한 유기 전기발광 소자는, 한쌍의 전극간에 1층 이상의 발광층을 포함하는 유기 기능층을 협지한 유기 전기발광 소자에 있어서, 상기 발광층이 상기 하기 화학식 1로 표시되는 옥사졸론 유도체로 이루어지는 유기 전기발광 소자 재료를 함유하는 층인 것을 특징으로 한다.The organic electroluminescent device according to claim 3 is an organic electroluminescent device in which an organic functional layer including one or more light emitting layers is sandwiched between a pair of electrodes, wherein the light emitting layer is formed of an oxazolone derivative represented by the following Chemical Formula 1 It is a layer containing an organic electroluminescent element material.
또한, 발광층은 450 나노미터 내지 590 나노미터의 파장에 전계 발광 스펙트럼을 갖는 녹색 발광 재료, 및 상기 화학식 1로 표시되는 옥사졸론 유도체로 이루어지는 유기 전기발광 소자 재료를 함유하는 층인 것을 특징으로 하는 층이도록 할 수 있다.In addition, the light emitting layer is a layer containing a green light emitting material having an electroluminescence spectrum at a wavelength of 450 nanometers to 590 nanometers, and an organic electroluminescent device material composed of an oxazolone derivative represented by the formula (1). can do.
또한, 발광층은 퀴놀린계 금속 착체, 및 상기 화학식 1로 표시되는 옥사졸론 유도체로 이루어지는 유기 전기발광 소자 재료를 함유하는 층이도록 할 수가 있다.The light emitting layer may be a layer containing a quinoline metal complex and an organic electroluminescent device material composed of an oxazolone derivative represented by the formula (1).
또한, 발광층은 퀴놀린 금속 착체, 및 상기 화학식 1로 표시되는 옥사졸론 유도체로 이루어지는 유기 전기발광 소자 재료를 함유하고, 상기 유기 전기발광 소자 재료를 상기 퀴놀린계 금속 착체에 대하여 0.001 중량%(wt%) 내지 50 중량%(wt%)의 범위에서 함유하도록 할 수가 있다.In addition, the light emitting layer contains a quinoline metal complex and an organic electroluminescent device material composed of an oxazolone derivative represented by Chemical Formula 1, and the organic electroluminescent device material is 0.001% by weight (wt%) based on the quinoline metal complex. It can be made to contain in the range of -50 weight% (wt%).
또한, 소정 기판상에 위쪽부터 음극, 발광층, 양극의 순서로 구비하도록 할 수가 있다.Furthermore, it can be provided in order of a cathode, a light emitting layer, and an anode from a top on a predetermined board | substrate.
또한, 소정 기판상에 위쪽부터 음극, 전자 수송층, 발광층, 정공 수송층, 양극의 순서로 구비하도록 할 수가 있다.It is also possible to provide a cathode, an electron transporting layer, a light emitting layer, a hole transporting layer, and an anode in the order above the predetermined substrate.
또한, 소정 기판상에 위쪽부터 음극, 발광층, 정공 수송층, 양극의 순서로 구비하도록 할 수가 있다.Further, on the predetermined substrate, it can be provided in the order of the cathode, the light emitting layer, the hole transport layer, and the anode in order.
또한, 소정 기판상에 위쪽부터 음극, 전자 수송층, 발광층, 양극의 순서로 구비하드록 할 수가 있다.Moreover, it can be provided on a predetermined board | substrate from the top in order of a cathode, an electron carrying layer, a light emitting layer, and an anode.
본 발명에 관한 유기 전기발광 소자 재료 및 그것을 사용한 유기 전기발광 소자에서는 유기 전기발광 소자 재료가 화학식 1로 표시되는 옥사졸론 유도체로 이루어지고, 한쌍의 전극간에 1층 이상의 발광층을 유기 기능층을 협지한 유기 전기발광 소자의 유기 기능층의 1층 이상을 형성하는 재료가 상기 유기 전기발광 소자 재료를 함유한다.In the organic electroluminescent device material and the organic electroluminescent device using the same according to the present invention, the organic electroluminescent device material is composed of an oxazolone derivative represented by the formula (1), and the organic functional layer is sandwiched between at least one light emitting layer between a pair of electrodes The material which forms one or more layers of the organic functional layer of an organic electroluminescent element contains the said organic electroluminescent element material.
이하, 본 발명의 유기 전기발광(EL) 소자의 실시 형태에 대하여 설명한다. 본 발명에서 사용되는 유기 EL 소자 재료를 구성하는 옥사졸론 유도체는 상기 종래의 문제점을 해결하는 특징을 갖는다. 즉, 본 발명의 유기 EL 소자 재료는 높은 양자 수율을 갖기 때문에 유기 EL 소자의 발광층 또는 발광층 중에 미량 혼입함으로써 적색 영역에서 높은 휘도로 발광시킬 수가 있다. 또한, 본 발명의 유기 전기발광 소자 재료는 저항 가열형의 성막법에 의해 용이하게 성막화가 가능하다. 덧붙여, 박막 성능은 매우 안정하며 평탄성이 우수하며, 대기중에 방치된 상태이더라도 결정화, 응집 상태 형성이라는 막 구조의 변화는 발견되지 않아 유기 EL 소자의 긴 수명을 도모하기가 용이하다.EMBODIMENT OF THE INVENTION Hereinafter, embodiment of the organic electroluminescent (EL) element of this invention is described. The oxazolone derivative constituting the organic EL device material used in the present invention has a feature that solves the above conventional problems. That is, since the organic EL device material of the present invention has a high quantum yield, it can emit light with high luminance in the red region by incorporating a small amount into the light emitting layer or the light emitting layer of the organic EL device. In addition, the organic electroluminescent device material of the present invention can be easily formed into a film by a resistive heating film forming method. In addition, the thin film performance is very stable and excellent in flatness, and even in the state of being left in the air, no change in the film structure such as crystallization and formation of agglomerated state is found, so that it is easy to achieve long life of the organic EL device.
본 발명에 관한 유기 EL 소자에서 사용하는 화학식 1로 표시되는 화합물의 예를 표 1에 나타냈다.Table 1 shows an example of the compound represented by the formula (1) used in the organic EL device of the present invention.
<화학식 1><Formula 1>
화학식 1로 표시되는 화합물은 이러한 예로 한정되는 것은 아니다.The compound represented by the formula (1) is not limited to this example.
또한, 본 발명에 관한 유기 EL 소자는 음극과 양극간에 유기 박막층을 1층 이상 적층한 구조이며, 그 예로서 도1 내지 도 4에 나타내는 바와 같이 이하의 4구조를 들 수가 있다.Moreover, the organic electroluminescent element which concerns on this invention is a structure which laminated | stacked one or more organic thin film layers between a cathode and an anode, As an example, as shown to FIG. 1 thru | or 4, the following four structures are mentioned.
(1)양극/발광층/음극(도1)(1) anode / light emitting layer / cathode (Fig. 1)
(2)양극/정공 수송층/발광층/전자 수송층/음극(도2)(2) Anode / hole transport layer / light emitting layer / electron transport layer / cathode (Fig. 2)
(3)양극/발광층/전자 수송층/음극(도3)(3) anode / light emitting layer / electron transport layer / cathode (Fig. 3)
(4)양극/정공 수송층/발광층/음극(도4)(4) anode / hole transport layer / light emitting layer / cathode (FIG. 4)
화학식 1로 표시되는 화합물은, 상기한 유기 EL 소자에서의 발광층을 사용할 수가 있다. 이 때 화학식 1로 표시되는 화합물에 덧붙여 다른 정공 수송 재료, 전자 수송 재료, 발광 재료와의 혼합물로서 사용하는 것도 가능하다. 본 발명에 관한 유기 EL 소자에 사용되는 정공 수송 재료는 특별히 한정되지 않으며, 통상 정공 수송 재료로서 사용되는 화합물이면 어떠한 화합물이어도 사용 가능하다.As the compound represented by the formula (1), the light emitting layer in the organic EL device described above can be used. In this case, it is also possible to use it as a mixture with another hole transport material, an electron transport material, and a luminescent material in addition to the compound represented by General formula (1). The hole transport material used for the organic EL device according to the present invention is not particularly limited, and any compound may be used as long as it is a compound normally used as the hole transport material.
예를 들면, 비스(디(p-톨릴)아미노페닐)-1,1-시클로헥산, N.N'-디페닐-N,N'-비스(3-메틸페닐)-1,1'-비페닐-4,4'-디아민, N.N'-디페닐-N-N-비스(1-나프틸)-(1,1'-비페닐)-4,4'-디아민, 스타 버스트형 분자 등을 들 수 있다.For example, bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane, N.N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl -4,4'-diamine, N.N'-diphenyl-NN-bis (1-naphthyl)-(1,1'-biphenyl) -4,4'-diamine, star burst type molecule | numerator, etc. are mentioned. Can be.
또한, 본 발명에 따른 유기 EL 소자에 사용되는 전자 수송 재료는 특별히 한정되지 않으며, 통상 전자 수송 재료로서 사용되고 있는 화합물이면 어떠한 전자 전송 재료라도 사용 가능하다. 예를 들면 2-(4-비페닐)-5-(4-t-부틸페닐)-1,3,4-옥사디아졸, 비스{2-(4-t-부틸페닐)-1,3,4-옥사디아졸}-m-페닐렌, 등의 옥사디아졸 유도체, 트리아졸 유도체, 옥사신 금속 착체 등을 들 수가 있다.In addition, the electron transport material used for the organic electroluminescent element which concerns on this invention is not specifically limited, Any electron transport material can be used as long as it is a compound normally used as an electron transport material. For example 2- (4-biphenyl) -5- (4-t-butylphenyl) -1,3,4-oxadiazole, bis {2- (4-t-butylphenyl) -1,3, Oxadiazole derivatives, such as 4-oxadiazole} -m-phenylene, a triazole derivative, an oxacin metal complex, etc. are mentioned.
<실시예><Example>
이하, 본 발명의 실시예의 제조 방법 또는 사용 방법에 관하여 구체적 수치 또는 구체적 제공 방법을 특정하고, 도면을 참조하여 본 발명 실시예의 동작을 하나씩 순서대로 상세히 설명한다.Hereinafter, specific numerical values or specific providing methods will be specified with respect to the manufacturing method or the method of using the embodiments of the present invention, and the operation of the embodiments of the present invention will be described in detail one by one with reference to the drawings.
유기 박막 EL 소자의 양극은 정공을 정공 수송층에 주입하는 역할을 담당하는 것이며, 4.5 eV 이상의 일함수를 갖는 것이 효과적이다. 본 발명에 관한 유기 EL 소자에 사용되는 양극 재료의 구체예로서는 산화 인듐 주석 합금(ITO), 산화 주석(NESA), 금, 은, 백금, 동 등이 있다. 또한, 음극으로서는 전자 수송층 또는 발광층에 전자를 효율좋게 도입하기 위하여 양극보다도 일함수가 작은 재료가 바람직하다. 음극 재료에 대하여 특별히 한정되지 않지만, 구체적으로는 인듐, 알루미늄, 마그네슘, 마그네슘-인듐 합금, 마그네슘-알루미늄 합금, 알루미늄-리튬 합금, 마그네슘-은 합금 등을 사용할 수가 있다.The anode of the organic thin film EL element plays a role of injecting holes into the hole transport layer, and it is effective to have a work function of 4.5 eV or more. Specific examples of the anode material used in the organic EL device according to the present invention include indium tin oxide alloy (ITO), tin oxide (NESA), gold, silver, platinum, copper and the like. As the cathode, a material having a lower work function than the anode is preferable in order to efficiently introduce electrons into the electron transporting layer or the light emitting layer. Although it does not specifically limit about a negative electrode material, Specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, magnesium-silver alloy, etc. can be used.
본 발명에 따른 유기 EL 소자에 따른 유기 EL 소자의 각 유기층의 형성 방법은 특별히 한정되지 않는다. 종래 공지된 진공 증착, 스핀코팅법에 의한 형성 방법을 들 수가 있다. 본 발명의 유기 EL 소자에 사용하는 화학식 1로 표시되는 유기 박막층은 진공 증착법, 분자선 증착법(MBE) 또는 용매에 녹인 용액의 침지법, 스핀코팅법, 캐스팅법, 바코드법, 롤코트법 등의 도포법에 의한 공지된 성막법으로 형성할 수가 있다. 본 발명에 따른 유기 EL 소자의 각 유기층의 막 두께는 특별히 한정되지 않지만, 일반적으로 막 두께가 너무 얇으면 핀홀 등의 결함이 발생되기 쉬우며, 반대로 너무 두꺼우면, 높은 인가 전압을 필요로 하게 되어 효율이 저하된다. 이 때문에 각 유기층의 막 두께는 1 nm 내지 1 ㎛의 범위가 바람직하다.The formation method of each organic layer of the organic electroluminescent element which concerns on the organic electroluminescent element which concerns on this invention is not specifically limited. The formation method by a conventionally well-known vacuum vapor deposition and spin coating method is mentioned. The organic thin film layer represented by Chemical Formula 1 used in the organic EL device of the present invention may be coated by vacuum deposition, molecular beam deposition (MBE) or dipping of a solution dissolved in a solvent, spin coating, casting, barcode, roll coating, or the like. It can form by the well-known film-forming method by the method. Although the film thickness of each organic layer of the organic electroluminescent element which concerns on this invention is not specifically limited, Generally, when a film thickness is too thin, defects, such as a pinhole, are easy to generate | occur | produce, On the contrary, when too thick, a high applied voltage is needed. The efficiency is lowered. For this reason, the film thickness of each organic layer has the preferable range of 1 nm-1 micrometer.
이하, 본 발명의 실시예에 대하여 설명하는데, 본 발명의 요지를 변경하지 않는 한 본 발명의 실시예로 한정되는 것은 아니다.Hereinafter, although the Example of this invention is described, it is not limited to the Example of this invention, unless the summary of this invention is changed.
(합성예)Synthesis Example
표 1중 화합물 (1) 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론의 합성Synthesis of Compound (1) 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone in Table 1
아세트산 나트륨(0.1 mol)의 존재하에, p-디메틸아미노벤즈알데히드(0.1 mol)와 히퓨린산(0.1 mol)을 무수 아세트산 중(500 ㎖)에서 2시간 환류하였다. 혼합물을 냉각하고, 석출된 결정을 톨루엔-헥산으로부터 재결정하여 82 %의 수율로 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론이 얻어졌다.In the presence of sodium acetate (0.1 mol), p-dimethylaminobenzaldehyde (0.1 mol) and hypurinic acid (0.1 mol) were refluxed in acetic anhydride (500 mL) for 2 hours. The mixture was cooled and the precipitated crystals were recrystallized from toluene-hexane to give 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone in a yield of 82%.
(실시예 1)(Example 1)
실시예 1에 따른 유기 EL 소자의 단면 구조를 도 5에 나타냈다. 본 실시예에 따른 유기 EL 소자는 유리 기판(1)과 유리 기판(1)상에 형성된 양극(2), 및 음극(3)과, 양극(2)과 음극(3)의 사이에 협지된 발광층(4)로 구성된다.The cross-sectional structure of the organic electroluminescent element which concerns on Example 1 is shown in FIG. The organic EL device according to the present embodiment includes a light emitting layer sandwiched between the glass substrate 1 and the anode 2 and the cathode 3 formed on the glass substrate 1 and between the anode 2 and the cathode 3. It consists of (4).
이하, 실시예 1에 따른 유기 EL 소자의 제작 순서에 대하여 설명한다, 우선, 유리 기판(1)상에 ITO를 스퍼터링에 의해 시트 저항 15 Ω/cm2이하가 되도록 성막하여 양극(2)으로 삼았다. 그 ITO가 부착된 유리를 순수한 물과 이소프로필알코올로 각각 약 40분간 초음파 세정을 행한 후, 다시 비등시킨 이소프로필알코올 상에서 건조시켰다. 다시 UV 오존 세정 장치로 이 기판을 10분간 세정하여 진공 증착 장치의 기판 홀더에 부착하였다.Hereinafter, the manufacturing procedure of the organic electroluminescent element which concerns on Example 1 is demonstrated. First, ITO was formed into a film on the glass substrate 1 so that sheet resistance might be 15 ohm / cm <2> or less by sputtering, and it was set as the anode 2. . The ITO-attached glass was ultrasonically cleaned for about 40 minutes with pure water and isopropyl alcohol, and then dried over boiled isopropyl alcohol. The substrate was then washed with a UV ozone cleaner for 10 minutes and attached to the substrate holder of the vacuum deposition apparatus.
또한, 고순도 그라파이트제의 도가니에 발광 재료인 상기 합성에서 얻은 4-4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론 1 g 넣고, 이것을 통전용 단자에 부착한 후, 진공층내를 2×10-4 Pa까지 배기하였다. 그리고, 발광 재료가 들어간 도가니에 통전하여 0.2 내지 0.3 nm/sec의 증착 속도로 60 nm의 막 두께가 될때까지 증착하였다. 이어서, 진공층을 대기압으로 되돌리고, 지지 기판/ITO/4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론층의 상부에 스테인리스제 증착 마스크를 부착하였다. 여기에서 BN제 보드에 알루미늄을 3 g 넣고, 통전용 단자에 부착하였다.In addition, 1 g of 4-4-methylaminobenzylidene) -2-phenyl-5-oxazolone obtained in the above-described synthesis as a light emitting material was placed in a crucible made of high purity graphite, which was attached to a terminal for energization, and then the inside of the vacuum layer was It exhausted to x10 <-4> Pa. Then, electricity was supplied to the crucible containing the light emitting material and deposited until the film thickness of 60 nm was reached at a deposition rate of 0.2 to 0.3 nm / sec. Subsequently, the vacuum layer was returned to atmospheric pressure, and a stainless steel deposition mask was attached on the support substrate / ITO / 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone layer. 3 g of aluminum was put into the board | substrate made from BN here, and it attached to the terminal for electricity supply.
마찬가지로, 텅스텐제의 필라멘트에 Li를 1 g 넣고, 다른 통전용 단자에 부착하였다. 진공층을 1×10-4 Pa까지 배기한 후, 알루미늄의 증착 속도가 0.2 nm/Sec가 되도록 통전하고, 동시에 리튬의 증착 속도가 0.02 nm/sec가 되도록 다른 증착 전원을 사용하여 통전하였다. 두가지 재료의 증착 속도가 안정해 졌을 때 셔터를 개방하고, 혼합막의 막 두께가 20 nm이 되었을 때 리튬의 증착 전원을 닫고, 알루미늄막을 170 nm의 막 두께가 될 때까지 성막하였다. 다시 진공층을 대기압으로 되돌리고, 지지 기판/ITO/4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론층 /AlLi/Al로 이루어지는 EL 소자를 제작하였다.Similarly, 1 g of Li was put in the tungsten filament, and it attached to the other terminal for electricity delivery. After evacuating the vacuum layer to 1 x 10 < -4 > Pa, it was energized so that the deposition rate of aluminum became 0.2 nm / Sec, and energized using another deposition power source so that the deposition rate of lithium became 0.02 nm / sec. The shutter was opened when the deposition rates of the two materials were stabilized, the deposition power of lithium was closed when the film thickness of the mixed film was 20 nm, and the aluminum film was formed until the film thickness was 170 nm. The vacuum layer was returned to atmospheric pressure again, and the EL element which consists of a support substrate / ITO / 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone layer / AlLi / Al was produced.
이 소자의 ITO를 양극, 알루미늄 전극을 음극으로 하여, 8 V 인가한 결과, 전류가 10 mA/㎠ 흐르고, 휘도 300 cd/㎡의 적색 발광을 얻었다. 이 때의 발광 효율은 1.1 루멘/와트(1 m/W)였다. 또한, 이 소자를 대기중에서 5000 시간 보존한 후, 비발광부 면적의 측정 결과, 발광 면적에 대한 비율은 9 %였다.When 8V was applied using ITO as the anode and the aluminum electrode as the cathode, the current flowed by 10 mA / cm 2, and red light emission with luminance of 300 cd / m 2 was obtained. The luminous efficiency at this time was 1.1 lumens / watt (1 m / W). After the device was stored in the air for 5000 hours, the ratio of the non-light emitting area was 9%.
이어서, 실시예 1에서 얻어진 효과에 대하여 설명한다. 본 발명의 일례인 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론은 재료 자체가 적색 영역에서 높은 형광의 양자 효율을 갖기 때문에, 유기 EL 소자의 발광 재료로서 사용했을 경우, 강한 형광을 얻을 수가 있다. 또한, 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론의 박막 상태는 안정하며, 장시간 유기 EL 소자를 구동하는 열적 부하를 부여하여도 무정형 상태를 유지할 수가 있다. 즉 유기 EL 소자의 덕스포트(비발광부) 형성을 강력히 억제한다고 할 수 있다.Next, the effect obtained in Example 1 is demonstrated. 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone, which is an example of the present invention, has high quantum efficiency of fluorescence in the red region, and thus is used as a light emitting material of an organic EL device. Strong fluorescence can be obtained. In addition, the thin film state of 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone is stable and can maintain an amorphous state even when a thermal load for driving an organic EL element is applied for a long time. That is, it can be said that the formation of the duck spot (non-light emitting part) of the organic EL element is strongly suppressed.
(실시예 2)(Example 2)
실시예 1과 마찬가지로 하여 ITO가 부착된 백판 유리를 증착기로 증착한 후, 고순도 그라파이트제의 도가니에 정공 수송층으로서 비스(디(p-톨릴)아미노페닐)-1,1-시클로헥산 1 g을 넣고, 별도 도가니에 발광 재료로서 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론 1 g을 넣었다. 진공층을 1×10-4 Pa까지 배기한 후, 비스(디(p-톨릴)아미노페닐)-1,1-시클로헥산이 들어간 도가니에 통전하여 0.2 내지 0.3 nm/sec의 증착 속도로 50 nm 의 막 두께가 될때까지 증착하였다.In the same manner as in Example 1, ITO-coated white glass was deposited by a vapor deposition machine, and then 1 g of bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane was added as a hole transporting layer to a crucible made of high purity graphite. Into the crucible, 1 g of 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone was added as a light emitting material. After evacuating the vacuum layer to 1 × 10-4 Pa, it is energized into a crucible containing bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane and 50 nm at a deposition rate of 0.2 to 0.3 nm / sec. It was deposited until the film thickness of.
이어서, 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론이 들어간 도가니에 통전하고, 증착 속도 0.2 내지 0.4 nm으로 막 두께 50 nm에 달할 때까지 성막하였다. 이어서, 진공층을 대기압으로 되돌리고, 지지 기판/ITO/비스(디(p-톨릴)아미노페닐)-1,1-시클로헥산층/4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론층의 구조의 소자에 실시예 1의 방법과 같은 수법에 의해 음극을 형성하였다.Subsequently, electricity was supplied to a crucible containing 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone, and a film was formed at a deposition rate of 0.2 to 0.4 nm until the film thickness reached 50 nm. Then, the vacuum layer was returned to atmospheric pressure, and the supporting substrate / ITO / bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane layer / 4- (4-methylaminobenzylidene) -2-phenyl-5 The cathode was formed in the element of the structure of an oxazolone layer by the method similar to the method of Example 1.
EL 소자를 증착기에서 꺼낸 후, 실시예 1의 경우와 마찬가지로 통전 시험을 행한 결과, 전압을 6 V 인가했을 때 10 mA/㎠의 전류가 흘러, 휘도 1000 cd/㎡의 적색 발광을 얻었다.After the EL element was taken out of the evaporator, a current-carrying test was conducted in the same manner as in Example 1, and when a voltage of 6 V was applied, a current of 10 mA / cm 2 flowed to obtain red light emission having a luminance of 1000 cd / m 2.
(실시예 3)(Example 3)
실시예 1의 경우와 마찬가지로 하여 준비한 ITO가 부착된 백판 유리를 증착기로 증착한 후, 고순도 그라파이트제의 도가니에 전자 수송층으로서 비스{2-(4-t-부틸페닐)-1,3,4-옥사디아졸}-m-페닐렌 1 g을 넣고, 별도 도가니에 발광 재료로서 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론 1 g을 넣었다. 진공층을 1×10-4 Pa까지 배기한 후, 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론이 들어간 도가니에 통전하여 0.2 내지 0.3 nm/sec의 증착 속도로 50 nm가 될 때까지 성막하였다.After depositing the white glass with ITO prepared in the same manner as in Example 1 with the evaporator, bis {2- (4-t-butylphenyl) -1,3,4- as an electron transporting layer in a crucible made of high purity graphite 1 g of oxadiazole} -m-phenylene was put, and 1 g of 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolones were put into the crucible separately. After evacuating the vacuum layer to 1 × 10 -4 Pa, it was energized into a crucible containing 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone at 50 at a deposition rate of 0.2 to 0.3 nm / sec. The film was formed until it became nm.
이어서, 비스{2-(4-t-부틸페닐)-1,3,4-옥사디아졸}-m-페닐렌이 들어간 도가니에 통전하고, 통전 속도 0.2 내지 0.4 nm에서 막 두께 50 nm이 될때까지 성막하였다. 이어서, 진공층을 대기압으로 되돌리고, 지지 기판/ITO/4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론/비스{2-(4-t-부틸페닐)-1,3,4-옥사디아졸}-m-페닐렌층의 구조의 소자에 실시예 1의 방법과 같은 수법에 의해 음극을 형성하였다.Subsequently, when a bis {2- (4-t-butylphenyl) -1,3,4-oxadiazole} -m-phenylene was supplied to the crucible, the thickness was 50 nm at a current passing rate of 0.2 to 0.4 nm. It was formed until. Then, the vacuum layer was returned to atmospheric pressure, and the supporting substrate / ITO / 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone / bis {2- (4-t-butylphenyl) -1,3 The negative electrode was formed in the element of the structure of the 4-4-diazadiazole} -m-phenylene layer by the method similar to the method of Example 1.
EL 소자를 증착기에서 꺼낸 후, 실시예 1의 경우와 마찬가지로 통전 시험을 행한 결과, 전압을 6 V 인가했을 때 6 mA/㎠의 전류가 흐르고, 휘도 220 cd/㎡의 적색 발광을 얻었다.After the EL element was taken out of the evaporator, a current-carrying test was conducted in the same manner as in Example 1, and when a voltage of 6 V was applied, a current of 6 mA / cm 2 flowed to obtain red light emission of luminance 220 cd / m 2.
(실시예 4)(Example 4)
실시예 1의 경우와 마찬가지로 하여 준비한 ITO가 부착된 백판 유리를 증착기로 증착한 후, 고순도 그라파이트제의 도가니에 정공 수송층으로서 비스(디(p-톨릴)아미노페닐)-1,1-시클로헥산 1 g을 넣고, 다시 별도의 도가니에 전자 수송 재료로서 비스{2-(4-t-부틸페닐)-1,3,4-옥사디아졸}-m-페닐렌 1 g을 넣고, 다시 별도 도가니에 발광 재료로서 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론 1 g을 넣었다.After depositing the white glass with ITO prepared in the same manner as in Example 1 with the evaporator, bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane 1 as a hole transporting layer in a crucible made of high purity graphite g was added, and 1 g of bis {2- (4-t-butylphenyl) -1,3,4-oxadiazole} -m-phenylene was added to a separate crucible again, and again in a separate crucible. 1 g of 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone was added as a light emitting material.
진공층을 1×10-4 Pa까지 배기한 후, 비스(디(p-톨릴)아미노페닐)-1,1-시클로헥산이 들어간 도가니에 통전하여 0.2 내지 0.3 nm/sec의 증착 속도로 40 nm가 될 때까지 성막하였다. 이어서, 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론이 들어간 도가니에 통전하고, 통전 속도 0.2 내지 0.3 nm의 증착 속도로 50 nm이 될때까지 성막하였다.After evacuating the vacuum layer to 1 × 10-4 Pa, it is energized into a crucible containing bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane and 40 nm at a deposition rate of 0.2 to 0.3 nm / sec. The tabernacle was made until. Subsequently, electricity was supplied to the crucible containing 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone and formed into a film at 50 nm at the deposition rate of 0.2-0.3 nm.
마지막으로 비스{2-(4-t-부틸페닐)-1,3,4-옥사디아졸}-m-페닐렌이 들어간 도가니에 통전하고 증착 속도 0.2 내지 0.4 nm에서 막 두께 50 nm이 될때까지 성막하였다. 이어서 진공층을 대기압으로 되돌리고, 지지 기판/ITO/비스(디(p-톨릴)아미노페닐)-1,1-시클로헥산/4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론층/비스{2-(4-t-부틸페닐)-1,3,4-옥사디아졸}-m-페닐렌층의 구조의 소자에 실시예 1의 방법과 같은 수법에 의해 음극을 형성하였다.Finally, a crucible containing bis {2- (4-t-butylphenyl) -1,3,4-oxadiazole} -m-phenylene was energized and the film thickness reached 50 nm at a deposition rate of 0.2 to 0.4 nm. The film was formed. The vacuum layer is then returned to atmospheric pressure and the supporting substrate / ITO / bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane / 4- (4-methylaminobenzylidene) -2-phenyl-5-oxa The cathode was formed in the element of the structure of a solon layer / bis {2- (4-t-butylphenyl) -1,3,4-oxadiazole} -m-phenylene layer by the same method as in Example 1. .
EL 소자를 증착기에서 꺼낸 후, 실시예 1의 경우와 마찬가지로 통전 시험을 행한 결과, 전압을 6 V 인가했을 때 15 mA/㎠의 전류가 흐르고, 휘도 4600 cd/㎡의 적색 발광을 얻었다.After the EL element was taken out of the evaporator, a current-carrying test was conducted in the same manner as in Example 1, and when a voltage of 6 V was applied, a current of 15 mA / cm 2 flowed to obtain red light emission of luminance 4600 cd / m 2.
(실시예 5)(Example 5)
실시예 1의 경우와 마찬가지로 지지 기판을 세정한 후, 증착 장치에 증착하고, 고순도 그라파이트제의 도가니에 정공 수송층으로서 비스(디(p-톨릴)아미노페닐)-1,1-시클로헥산 1 g을 넣고, 다시 별도의 도가니에 발광 호스트 재료로서 비스스티릴안트라센 유도체(BSA) 1 g을 넣었다. 다시 별도의 도가니에 발광 도판트제로서 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론 1 g을 넣고, 각각 별도의 통전용 단자에 부착하였다. 또한, 별도의 도가니에 전자 수송체로서 비스{2-(4-t-부틸페닐)-1,3,4-옥사디아졸}-m-페닐렌 1 g을 넣고, 앞서의 통전용 단자와는 별도의 단자에 부착하였다.In the same manner as in Example 1, the supporting substrate was cleaned, and then deposited on a vapor deposition apparatus, and 1 g of bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane was added as a hole transporting layer to a crucible made of high purity graphite. Then, 1 g of bisstyrylanthracene derivative (BSA) was placed in a separate crucible as a light emitting host material. Again, 1 g of 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone was put as a light emitting dopant in a separate crucible, and each was attached to a separate power supply terminal. In addition, 1 g of bis {2- (4-t-butylphenyl) -1,3,4-oxadiazole} -m-phenylene was put as an electron transporter in a separate crucible, Attached to a separate terminal.
진공층내를 1×10-4 Pa까지 배기한 후, 비스(디(p-톨릴)아미노페닐)-1,1-시클로헥산이 들어간 도가니에 통전하여 0.2 내지 0.3 nm/sec의 증착 속도로 50 nm가 될 때까지 성막하였다. 이어서, BSA 및 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론이 들어간 도가니에 통전하고, BSA가 0.2 내지 0.3 nm/sec, 그리고 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론이 0.01 내지 0.02 nm/sec가 되도록 전류를 제어하여 양자가 안정해졌을 무렵에 동시에 증착을 개시하였다.After evacuating the inside of the vacuum layer to 1 × 10 -4 Pa, it was energized into a crucible containing bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane and 50 nm at a deposition rate of 0.2 to 0.3 nm / sec. The tabernacle was made until. Subsequently, electricity was supplied to a crucible containing BSA and 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone, and the BSA was 0.2 to 0.3 nm / sec, and 4- (4-methylaminobenzylidene) The deposition was started at the same time when both were stabilized by controlling the current so that the 2-phenyl-5-oxazolone was 0.01 to 0.02 nm / sec.
BSA의 막 두께가 20 nm 성막된 단계에서 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론층의 통전을 멈추고, BSA만의 막을 계속해서 30 nm 성막하였다. 이어서, 비스{2-(4-t-부틸페닐)-1,3,4-옥사디아졸}-m-페닐렌이 들어간 도가니에 통전하여 증착 속도 0.2 내지 0.4 nm에서 막 두께 50 nm이 될때까지 성막하였다.At the stage where the film thickness of BSA was formed into 20 nm, the energization of the 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone layer was stopped, and the BSA-only film was continued to form 30 nm. Then, a crucible containing bis {2- (4-t-butylphenyl) -1,3,4-oxadiazole} -m-phenylene was energized until the film thickness was 50 nm at a deposition rate of 0.2 to 0.4 nm. The film was formed.
이렇게 하여 제작된 지지 기판/ITO/비스(디(p-톨릴)아미노페닐)-1,1-시클로헥산층/BSA+4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론/BSA/비스{2-(4-t-부틸페닐)-1,3,4-옥사디아졸}-m-페닐렌층의 구조를 갖는 소자에 다시 실시예 1의 경우와 마찬가지 방법에 의해 음극을 형성하였다.Supporting substrate / ITO / bis (di (p-tolyl) aminophenyl) -1,1-cyclohexane layer / BSA + 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone thus produced The cathode having a structure of a / BSA / bis {2- (4-t-butylphenyl) -1,3,4-oxadiazole} -m-phenylene layer was again prepared by the same method as in Example 1 Formed.
그리고, 실시예 1의 경우와 마찬가지로 통전 시험을 행한 결과, 인가 전압 5 V일때, 전류 밀도 10 mA/㎠에 상당하는 전류가 흐르고 1200 cd/㎡의 적색 발광이 얻어졌다. 이 소자를 질소 중에서 5 mA/㎠의 전류 밀도에서 구동 시험을 행하여 휘도의 반감 시간을 측정했더니 약 1000시간이었다.As a result of conducting an energization test as in the case of Example 1, when the applied voltage was 5 V, a current corresponding to a current density of 10 mA / cm 2 flowed and red light emission of 1200 cd / m 2 was obtained. The device was subjected to a driving test at a current density of 5 mA / cm 2 in nitrogen, and the half life time of the luminance was measured, and it was about 1000 hours.
(실시예 6 내지 10)(Examples 6 to 10)
발광 호스트 재료를 8-퀴놀리놀알루미늄 착체로서 사용한 것 이외는 실시예 5의 경우와 같은 방법으로 EL 소자를 제작하였다. 또한 이 때, 각 실시예마다 표 2에 나타낸 바와 같은 발광 호스트 재료와 도판트 재료와의 중량비의 조건하에서 제작하였다. 이러한 소자에 대히여 실시예 1의 경우와 마찬가지로 통전 시험을 행함과 동시에 질소 중에서의 전류 밀도 5 mA/㎠의 진공 조건에서 휘도의 반감 시간을 측정하였다. 그 결과, 표 2에 나타내는 바와 같이 이러한 제작 조건하에서는 효율, 구동 수명이 우수한 소자를 얻을 수가 있었다.An EL device was fabricated in the same manner as in the fifth embodiment except that a light emitting host material was used as the 8-quinolinol aluminum complex. At this time, each Example was produced under the conditions of the weight ratio of the light emitting host material and the dopant material as shown in Table 2. In the same manner as in Example 1, the half-life time of the luminance was measured at the same time as in the case of Example 1 and under vacuum conditions of a current density of 5 mA / cm 2 in nitrogen. As a result, as shown in Table 2, under these production conditions, an element having excellent efficiency and driving life was obtained.
(실시예 11)(Example 11)
정공 수송 재료를 N'-디페닐-N,N'-ㅂ비스(3-메틸페닐)-1,1'-04비페닐-4,4'-디아민으로 한 것 이외는 실시예 2의 경우와 같은 방법으로 유기 EL 소자를 제작하였다. 이 소자에 대하여 실시예 1의 경우와 마찬가지로 통전 시험을 행했더니 6V 인가시에 전류 밀도 15 mA/㎠에 상당하는 전류가 흐르고, 휘도 약 2800 cd/㎡의 적색 발광이 얻어졌다.As in the case of Example 2, except that the hole transport material was N'-diphenyl-N, N'-bisbis (3-methylphenyl) -1,1'-04biphenyl-4,4'-diamine. An organic EL device was produced by the method. When a current-carrying test was conducted on the device in the same manner as in Example 1, a current corresponding to a current density of 15 mA / cm 2 flowed when 6 V was applied, and red light emission of luminance about 2800 cd / m 2 was obtained.
(실시예 12)(Example 12)
정공 수송 재료를 N,N'-디페닐-N-N-비스(1-나프틸)-(1,1'-비페닐)-4,4'-디아민으로 한 것 이외는 실시예 2의 경우와 같은 방법으로 유기 El 소자를 제작하였다. 이 소자에 대하여 실시예 1의 경우와 마찬가지로 통전 시험을 행했더니 6V 인가시에 전류 밀도 10 mA/㎠에 상당하는 전류가 흐르고, 휘도 약 2400 cd/㎡의 적색 발광이 얻어졌다.As in Example 2, except that the hole transport material was N, N'-diphenyl-NN-bis (1-naphthyl)-(1,1'-biphenyl) -4,4'-diamine An organic El device was produced by the method. When a current-carrying test was conducted on the device in the same manner as in Example 1, when 6V was applied, a current corresponding to a current density of 10 mA / cm 2 flowed, and red light emission of about 2400 cd / m 2 was obtained.
(실시예 13)(Example 13)
전자 수송 재료를 2-(4-비페닐)-5-(4-t-부틸페닐)-1,3,4-옥사디아졸로 한 것 이외는 실시예 3의 경우와 같은 방법으로 유기 EL 소자를 제작하였다. 이 소자에 대하여 실시예 1의 경우와 마찬가지로 통전 시험을 행했더니 6V 인가시에 전류 밀도 10 mA/㎠에 상당하는 전류가 흐르고, 휘도 약 2400 cd/㎡의 적색 발광이 얻어졌다.An organic EL device was prepared in the same manner as in Example 3, except that the electron transporting material was 2- (4-biphenyl) -5- (4-t-butylphenyl) -1,3,4-oxadiazole. Produced. When a current-carrying test was conducted on the device in the same manner as in Example 1, when 6V was applied, a current corresponding to a current density of 10 mA / cm 2 flowed, and red light emission of about 2400 cd / m 2 was obtained.
(실시예 14)(Example 14)
정공 수송 재료를 N'-디페닐-N,N'-비스(3-메틸페닐)-1,1'-비페닐-4,4'-디아민, 전자 수송 재료를 2-(4-비페닐)-5-(4-t-부틸페닐)-1,3,4-옥사디아졸로 한 것 이외는 실시예 4의 경우와 같은 방법으로 유기 EL 소자를 제작하였다. 이 소자에 대하여 실시예 1의 경우와 마찬가지로 통전 시험을 행했더니 6V 인가시에 전류 밀도 20 mA/㎠에 상당하는 전류가 흐르고, 휘도 약 4800 cd/㎡의 적색 발광이 얻어졌다.N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1'-biphenyl-4,4'-diamine for hole transport material, 2- (4-biphenyl)-for electron transport material An organic EL device was manufactured in the same manner as in Example 4 except for using 5- (4-t-butylphenyl) -1,3,4-oxadiazole. When a current-carrying test was conducted on this device as in the case of Example 1, a current corresponding to a current density of 20 mA / cm 2 flowed when 6V was applied, and red light emission of luminance about 4800 cd / m 2 was obtained.
(실시예 15)(Example 15)
정공 수송 재료를 N,N'-비페닐-N,N-비스(1-나프틸)-(1,1'-비페닐)-4,4'-디아민, 전자 수송 재료를 2-(4-비페닐)-5-(4-t-부틸페닐)-1,3,4-옥사디아졸로 한 것 이외는 실시예 4의 경우와 같은 방법으로 유기 EL 소자를 제작하였다. 이 소자에 대하여 실시예 1의 경우와 마찬가지로 통전 시험을 행했더니 6V 인가시에 전류 밀도 20 mA/㎠에 상당하는 전류가 흐르고, 휘도 약 3600 cd/㎡의 적색 발광이 얻어졌다.N, N'-biphenyl-N, N-bis (1-naphthyl)-(1,1'-biphenyl) -4,4'-diamine for the hole transport material, 2- (4- An organic EL device was manufactured in the same manner as in Example 4 except for using biphenyl) -5- (4-t-butylphenyl) -1,3,4-oxadiazole. When a current-carrying test was conducted on the device in the same manner as in Example 1, a current corresponding to a current density of 20 mA / cm 2 flowed when 6V was applied, and red light emission of luminance about 3600 cd / m 2 was obtained.
(실시예 16)(Example 16)
발광 재료를 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론으로 한 것 이외는 실시예 1의 경우와 같은 방법으로 유기 EL 소자를 제작하였다. 이 소자에 대하여 실시예 1의 경우와 마찬가지로 통전 시험을 행했더니 6V 인가시에 전류 밀도 2 mA/㎠에 상당하는 전류가 흐르고, 휘도 약 40 cd/㎡의 적색 발광이 얻어졌다.An organic EL device was fabricated in the same manner as in Example 1 except that the light emitting material was 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone. When a current-carrying test was conducted on the device in the same manner as in Example 1, a current corresponding to a current density of 2 mA / cm 2 flowed when 6V was applied, and red light emission of about 40 cd / m 2 was obtained.
(실시예 17)(Example 17)
발광 재료를 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론으로 한 것 이외는 실시예 2의 경우와 같은 방법으로 유기 EL 소자를 제작하였다. 이 소자에 대하여 실시예 1의 경우와 마찬가지로 통전 시험을 행했더니 6V 인가시에 전류 밀도 5 mA/㎠에 상당하는 전류가 흐르고, 휘도 약 55 cd/㎡의 적색 발광이 얻어졌다.An organic EL device was manufactured in the same manner as in Example 2, except that the light emitting material was 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone. When a current-carrying test was conducted on the device in the same manner as in Example 1, when 6V was applied, a current corresponding to a current density of 5 mA / cm 2 flowed, and red light emission with a luminance of about 55 cd / m 2 was obtained.
(실시예 18)(Example 18)
발광 재료를 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론으로 한 것 이외는 실시예 3의 경우와 같은 방법으로 유기 EL 소자를 제작하였다. 이 소자에 대하여 실시예 1의 경우와 마찬가지로 통전 시험을 행했더니 6V 인가시에 전류 밀도 2 mA/㎠에 상당하는 전류가 흐르고, 휘도 약 70 cd/㎡의 적색 발광이 얻어졌다.An organic EL device was manufactured in the same manner as in Example 3, except that the light emitting material was 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone. When a current-carrying test was conducted on the device in the same manner as in Example 1, a current corresponding to a current density of 2 mA / cm 2 flowed when 6V was applied, and red light emission with a luminance of about 70 cd / m 2 was obtained.
(실시예 19)(Example 19)
발광 재료를 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론으로 한 것 이외는 실시예 4의 경우와 같은 방법으로 유기 EL 소자를 제작하였다. 이 소자에 대하여 실시예 1의 경우와 마찬가지로 통전 시험을 행했더니 6V 인가시에 전류 밀도 2 mA/㎠에 상당하는 전류가 흐르고, 휘도 약 40 cd/㎡의 적색 발광이 얻어졌다.An organic EL device was produced in the same manner as in Example 4 except that the light emitting material was 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone. When a current-carrying test was conducted on the device in the same manner as in Example 1, a current corresponding to a current density of 2 mA / cm 2 flowed when 6V was applied, and red light emission of about 40 cd / m 2 was obtained.
(실시예 20)(Example 20)
발광 재료를 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론으로 하고, 정공 수송 재료를 N'-디페닐-N,N'-비스(3-메틸페닐)-1,1'-비페닐-4,4'-디아민으로 한 것 이외는 실시예 2의 경우와 같은 방법으로 유기 EL 소자를 제작하였다. 이 소자에 대하여 실시예 1의 경우와 마찬가지로 통전 시험을 행했더니 6V 인가시에 전류 밀도 4 mA/㎠에 상당하는 전류가 흐르고, 휘도 약 80 cd/㎡의 적색 발광이 얻어졌다.The light emitting material was 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone, and the hole transport material was N'-diphenyl-N, N'-bis (3-methylphenyl) -1,1 An organic EL device was fabricated in the same manner as in Example 2 except for using '-biphenyl-4,4'-diamine. When a current-carrying test was conducted on the device in the same manner as in Example 1, a current corresponding to a current density of 4 mA / cm 2 flowed when 6V was applied, and red light emission of luminance about 80 cd / m 2 was obtained.
(실시예 21)(Example 21)
발광 재료를 4-(4-메틸아미노벤질리덴)-2-페닐-5-옥사졸론으로 하고, 전자 수송 재료를 2-(4-비페닐)-5-(4-t-부틸페닐)-1,3,4-옥사다아졸로 한 것 이외는 실시예 3의 경우와 같은 방법으로 유기 EL 소자를 제작하였다. 이 소자에 대하여 실시예 1의 경우와 마찬가지로 통전 시험을 행했더니 6V 인가시에 전류 밀도 4 mA/㎠에 상당하는 전류가 흐르고, 휘도 약 100 cd/㎡의 적색 발광이 얻어졌다.The light emitting material was 4- (4-methylaminobenzylidene) -2-phenyl-5-oxazolone, and the electron transporting material was 2- (4-biphenyl) -5- (4-t-butylphenyl) -1. An organic EL device was fabricated in the same manner as in the case of Example 3 except for using 3,4-oxadiazole. When a current-carrying test was conducted on the device in the same manner as in Example 1, when 6V was applied, a current corresponding to a current density of 4 mA / cm 2 flowed, and red light emission of luminance about 100 cd / m 2 was obtained.
또한, 화학식 1로 표시되는 유기 EL 소자 재료는 발광층내에서 퀴놀린계 금속 착체 등의 호스트 물질에 대히여 0.001 중량%(wt%) 내지 50 중량%(wt%)의 범위에서 함유하도록 하는 것이 바람직하다.In addition, the organic EL device material represented by the formula (1) is preferably contained in the light emitting layer in the range of 0.001% by weight (wt%) to 50% by weight (wt%) relative to the host material such as quinoline-based metal complex. .
이상과 같이, 본 발명에 관한 유기 전기발광 소자 재료 및 그것을 사용한 유기 전기발광 소자가 화학식 1로 표시되는 옥사졸론 유도체로 이루어지며, 한쌍의 전극간에 1층 이상의 발광층을 포함하는 유기 기능층을 협지한 유기 전기발광 소자의 유기 기능층의 1층 이상을 구성하는 재료가 상기 유기 전기발광 소자 재료를 함유하도록 한 것으로, 발광층을 적색 영역에서 높은 휘도로 발광시킴과 동시에 긴 수명을 가질 수 있다.As mentioned above, the organic electroluminescent element material which concerns on this invention, and the organic electroluminescent element using the same consist of the oxazolone derivative represented by General formula (1), and sandwiched the organic functional layer containing one or more light emitting layers between a pair of electrodes. The material constituting at least one layer of the organic functional layer of the organic electroluminescent device contains the organic electroluminescent device material, and the light emitting layer can emit light with high luminance in the red region and have a long lifetime.
Claims (17)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP10092223A JP3092583B2 (en) | 1998-03-23 | 1998-03-23 | Organic electroluminescent device material and organic electroluminescent device using the same |
| JP98-092223 | 1998-03-23 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| KR19990078127A true KR19990078127A (en) | 1999-10-25 |
Family
ID=14048452
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| KR1019990009762A KR19990078127A (en) | 1998-03-23 | 1999-03-23 | Organic Electroluminescence Material and Device Using the Same |
Country Status (3)
| Country | Link |
|---|---|
| JP (1) | JP3092583B2 (en) |
| KR (1) | KR19990078127A (en) |
| TW (1) | TW417407B (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100528905B1 (en) * | 1999-04-30 | 2005-11-16 | 삼성에스디아이 주식회사 | light-emitting compound, display device employing the same as color developing substance |
| KR100577179B1 (en) * | 2001-10-30 | 2006-05-10 | 엘지전자 주식회사 | Organic Electroluminescent Element |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US6899961B2 (en) * | 1999-12-15 | 2005-05-31 | Samsung Sdi Co., Ltd. | Organic electroluminescence device |
| CN100453533C (en) * | 2003-12-12 | 2009-01-21 | 中国科学院上海药物研究所 | Acceptor excitant of a class of pancreas hyperglycemia peptide-1, preparation method and usage |
-
1998
- 1998-03-23 JP JP10092223A patent/JP3092583B2/en not_active Expired - Fee Related
-
1999
- 1999-03-22 TW TW088104484A patent/TW417407B/en active
- 1999-03-23 KR KR1019990009762A patent/KR19990078127A/en active IP Right Grant
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| KR100528905B1 (en) * | 1999-04-30 | 2005-11-16 | 삼성에스디아이 주식회사 | light-emitting compound, display device employing the same as color developing substance |
| KR100577179B1 (en) * | 2001-10-30 | 2006-05-10 | 엘지전자 주식회사 | Organic Electroluminescent Element |
Also Published As
| Publication number | Publication date |
|---|---|
| TW417407B (en) | 2001-01-01 |
| JP3092583B2 (en) | 2000-09-25 |
| JPH11273865A (en) | 1999-10-08 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US5779937A (en) | Organic electroluminescent device | |
| EP1010742B1 (en) | Green organic electroluminescent devices | |
| EP0825803B1 (en) | Electron transporting materials for organic electroluminescent devices | |
| US7736758B2 (en) | Light emitting device having dopants in a light emitting layer | |
| JP4623223B2 (en) | Organic EL device | |
| EP1084127B1 (en) | Organometallic complex molecule and organic electroluminescent device using the same | |
| JP3650552B2 (en) | Organic electroluminescence device and panel using the same | |
| JP2006303527A (en) | Highly transparent non-metallic cathode | |
| JP2005166680A (en) | Organic el element | |
| EP1195422A1 (en) | Thin film el device | |
| JP3575335B2 (en) | Organic light emitting device | |
| JP3092583B2 (en) | Organic electroluminescent device material and organic electroluminescent device using the same | |
| JP4057250B2 (en) | Organic EL element and organic EL display | |
| JP2004047493A (en) | Organic light emitting element | |
| EP1809077A2 (en) | Organic electroluminescent element | |
| KR100354861B1 (en) | Organic electroluminescent device | |
| JP3452128B2 (en) | Organic electroluminescence device | |
| JP3206741B2 (en) | Organic electroluminescence device | |
| JP3525434B2 (en) | Organic electroluminescence device | |
| JP2004091382A (en) | Organometallic complex and organic electroluminescent element using the same | |
| JPH05279662A (en) | Organic electroluminescent element |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A201 | Request for examination | ||
| E701 | Decision to grant or registration of patent right | ||
| NORF | Unpaid initial registration fee |