TWI260339B - Organometallic compound and organic electroluminescent device including the same - Google Patents
Organometallic compound and organic electroluminescent device including the same Download PDFInfo
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- TWI260339B TWI260339B TW093130362A TW93130362A TWI260339B TW I260339 B TWI260339 B TW I260339B TW 093130362 A TW093130362 A TW 093130362A TW 93130362 A TW93130362 A TW 93130362A TW I260339 B TWI260339 B TW I260339B
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- alkoxy
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- 150000002902 organometallic compounds Chemical class 0.000 title 1
- 125000003118 aryl group Chemical group 0.000 claims abstract description 16
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 15
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 12
- 125000002524 organometallic group Chemical group 0.000 claims abstract description 12
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 11
- 125000004404 heteroalkyl group Chemical group 0.000 claims abstract description 9
- 125000005843 halogen group Chemical group 0.000 claims abstract description 8
- 150000002367 halogens Chemical class 0.000 claims abstract description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 6
- 229910052723 transition metal Inorganic materials 0.000 claims abstract description 6
- 150000003624 transition metals Chemical class 0.000 claims abstract description 6
- 125000006651 (C3-C20) cycloalkyl group Chemical group 0.000 claims abstract 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 14
- 229910052741 iridium Inorganic materials 0.000 claims description 8
- 239000000463 material Substances 0.000 claims description 6
- 229910052707 ruthenium Inorganic materials 0.000 claims description 6
- 150000004696 coordination complex Chemical class 0.000 claims description 5
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 5
- 239000000126 substance Substances 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 3
- 229910052702 rhenium Inorganic materials 0.000 claims description 3
- 238000005401 electroluminescence Methods 0.000 claims description 2
- 229910052697 platinum Inorganic materials 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Natural products C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims 1
- 239000002019 doping agent Substances 0.000 claims 1
- 239000007789 gas Substances 0.000 claims 1
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims 1
- 229940028444 muse Drugs 0.000 claims 1
- 229910052762 osmium Inorganic materials 0.000 claims 1
- GMVPRGQOIOIIMI-DWKJAMRDSA-N prostaglandin E1 Chemical compound CCCCC[C@H](O)\C=C\[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCC(O)=O GMVPRGQOIOIIMI-DWKJAMRDSA-N 0.000 claims 1
- SQQWBSBBCSFQGC-JLHYYAGUSA-N ubiquinone-2 Chemical compound COC1=C(OC)C(=O)C(C\C=C(/C)CCC=C(C)C)=C(C)C1=O SQQWBSBBCSFQGC-JLHYYAGUSA-N 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 2
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 150000001875 compounds Chemical class 0.000 description 12
- 239000010410 layer Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 8
- 238000004020 luminiscence type Methods 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- -1 t-butyl aCaC Chemical compound 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 4
- BTBUEUYNUDRHOZ-UHFFFAOYSA-N Borate Chemical compound [O-]B([O-])[O-] BTBUEUYNUDRHOZ-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical group [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- 239000000539 dimer Substances 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 239000003446 ligand Substances 0.000 description 4
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 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 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- 239000002244 precipitate Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- 229910052708 sodium Inorganic materials 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 229910000029 sodium carbonate Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- ZLGVZKQXZYQJSM-UHFFFAOYSA-N 1,2-diphenylbenzimidazole Chemical compound C1=CC=CC=C1C1=NC2=CC=CC=C2N1C1=CC=CC=C1 ZLGVZKQXZYQJSM-UHFFFAOYSA-N 0.000 description 2
- NFCPRRWCTNLGSN-UHFFFAOYSA-N 2-n-phenylbenzene-1,2-diamine Chemical compound NC1=CC=CC=C1NC1=CC=CC=C1 NFCPRRWCTNLGSN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000008367 deionised water Substances 0.000 description 2
- 229910021641 deionized water Inorganic materials 0.000 description 2
- INLXGFGSOCSZOT-UHFFFAOYSA-N di(pyrazol-1-yloxy)borinic acid Chemical compound C1=CC=NN1OB(O)ON1C=CC=N1 INLXGFGSOCSZOT-UHFFFAOYSA-N 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- LNJXVUXPFZKMNF-UHFFFAOYSA-K iridium(3+);trichloride;trihydrate Chemical compound O.O.O.Cl[Ir](Cl)Cl LNJXVUXPFZKMNF-UHFFFAOYSA-K 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 238000005424 photoluminescence Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000005215 recombination Methods 0.000 description 2
- 230000006798 recombination Effects 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000000859 sublimation Methods 0.000 description 2
- 230000008022 sublimation Effects 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical compound NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- XXRCUYVCPSWGCC-UHFFFAOYSA-N Ethyl pyruvate Chemical compound CCOC(=O)C(C)=O XXRCUYVCPSWGCC-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- CMJGTBTWHDECJU-UHFFFAOYSA-N OBON1C=CC=N1 Chemical compound OBON1C=CC=N1 CMJGTBTWHDECJU-UHFFFAOYSA-N 0.000 description 1
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 229940125904 compound 1 Drugs 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000012217 deletion Methods 0.000 description 1
- 230000037430 deletion Effects 0.000 description 1
- 230000005684 electric field Effects 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 125000006575 electron-withdrawing group Chemical group 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 1
- 238000002189 fluorescence spectrum Methods 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 125000002883 imidazolyl group Chemical group 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000000468 ketone group Chemical group 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- SIOXPEMLGUPBBT-UHFFFAOYSA-M picolinate Chemical compound [O-]C(=O)C1=CC=CC=N1 SIOXPEMLGUPBBT-UHFFFAOYSA-M 0.000 description 1
- VLRICFVOGGIMKK-UHFFFAOYSA-N pyrazol-1-yloxyboronic acid Chemical compound OB(O)ON1C=CC=N1 VLRICFVOGGIMKK-UHFFFAOYSA-N 0.000 description 1
- 239000013049 sediment Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
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- 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
- H10K85/30—Coordination compounds
- H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
- H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
- C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
- C07F15/0033—Iridium compounds
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- 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
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- H—ELECTRICITY
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
- H10K71/80—Manufacture or treatment specially adapted for the organic devices covered by this subclass using temporary substrates
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- 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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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1022—Heterocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
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- 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
- C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K2101/00—Properties of the organic materials covered by group H10K85/00
- H10K2101/10—Triplet emission
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- H10K2102/00—Constructional details relating to the organic devices covered by this subclass
- H10K2102/301—Details of OLEDs
- H10K2102/311—Flexible OLED
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
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- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
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- H10K59/12—Active-matrix OLED [AMOLED] displays
- H10K59/1201—Manufacture or treatment
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- 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
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- Microelectronics & Electronic Packaging (AREA)
- Electroluminescent Light Sources (AREA)
Description
1260339 九、發明說明： 【發明所屬之技術領域】 本發明有關一種用於有機電致發光裝置之有機金屬錯合 物，特別有關於一種有機金屬錯合物，其可作為有機電致發光 裝置之有機發光介質層。 x 【先前技術】 有機電致發光裝置(organic electiOluminescent device)，亦稱作有 機發光二極體(organic light-emitting diode; 0LED)，是以有機層作為 主動層的一種發光二極體(LED)。由於有機電致發光裝置具有低電壓操作、 高亮度、重量輕、廣視角、以及高對比值等優點，近年來已漸漸使用於平 面面板顯示器（flat panel display)上。 一般而言，0LED包括一對電極，以及在電極之間的一有機發光介質層。 發光是導因於以下的現象。當電場施於兩電極時，陰極射出電子到有機發 光介質層，陽極射出電洞到有機發光介質層。當電子與電洞在有機發光介 質層内結合時，會產生激子(excitons)。電子和電洞的再結合就伴隨著發 光。 依據電洞和電子的自旋態（spin state)，由電洞和電子之再結合而產 生的激子可具有三重態（triplet)或單重態（singlet)之自旋態。由單重態 激子（singlet exciton)所產生的發光為螢光（fluorescence)，而由三重態 激子（triplet exciton)所產生的發光為碟光(phosphorescence)。碟光的 發光效率是螢光的三倍。因此，發展高效率的磷光材料以增進〇LED的發光 效率是非常重要的。 已有些有機金屬錯合物被報導出來具有很強的鱗光(Lgjj^nsky，et al·，Inorganic Chemistry，2001，40，1704)，並且利用這些錯合物來製 造有效的0LED’在綠色到紅色的範圍内發光(Lamansky，etal.，J. Am. Chem. 1260339
Soc·，2001’ 123，4304)。美國專利申請案公開第20030072964A1號中揭 鉻種4光之有機金屬錯合物，其包括phenylquin〇Hnate配位基。美國 專利申晴案公開第·GG2觀Al、2G_182441A卜誦G116788A1及 200401Q2632A1就，亦有揭露其他發光之有機金屬錯合物。美國專利第 6, 687, 266號揭示一種發光材料，具有下列配位基：
或是具有下列結構：
η 其揭示X較佳例為乙酿丙酮酸根(aCetylacet〇nate，· acac)、㈣甲酸根 (picolinate ; pic)、及 dipivaloylmetanate (第三丁基 acac ; t—butyl aCaC)，均具有酮基(=0)，做為輔助配位基(ancillary ligand)。或者另一 實施例為m為3，及η為〇。 然而，對於發綠光之有機金屬錯合物，仍有相當大的發展需求。 【發明内容】 本發明提供一種有機金屬錯合物，具有下列化學式（丨）或（π) ·· 1260339
其中 ⑴ (II) Μ為一過渡金屬； R1為Η、顧原子、Ci，烷基 -20 雜芳香基、或Cs,環垸基· 、元氧基、C3_18雜燒基、C3,芳香基、C3-: 每個R2為相同或不同， 芳香基、C3,雜芳香基、戋c财—1-18垸基、Cl~18燒氧基、C3,雜烷基、 接之碳原子共同形成4 2 °長烷基，或者兩個R2連接在一起而與其所連 备個i?心 4員之芳香環或雜芳香環； 母個R為相同或不同，且為 — 辛、「卩 馬H CN、二氰乙烯基(tricyanovinyi)、鹵 : 8烧基Cl，丈元氧基、C3_18雜絲、G-2。芳香基、C3-2G雜芳香基、 或“環燒基，其中X為鹵素；及 每個R為Η、C"烷基、Ci-3烷氧基、或經!I素(F、a、Br)取代之(：1-3烷 基0 本發明又提供一種有機電致發光裝置，其包括一對電極，以及在此對 電極之間的—有機發光介質層，其中此有機發光介質層包括一如上述之有 機金屬錯合物。 【實施方式】 1260339 本發明提供一種含有啼°坐配位基（imidazole 1 igand)及四卩比嗤删或雙 吡唑配位基之有機金屬錯合物，具有化學式（I)或（II):
在化學式（I)或（II)中，Μ為一過渡金屬，最好是具有/電子執域的過 渡金屬’例如但不限於：Ir，Pt，〇s，Re，Ru，或此，較佳為卜。 R為Η、鹵原子、Cu烷基、Cu烷氧基、(^18雜烷基、芳香基、Cs_20 雜方香基、或C3,環烷基。較佳情況為，R1為推電子基(electr〇n—d〇nati职 group)，例如Cl_18烷基，Cm8烧氧基，或c3 i8雜烧基。推電子基之代表性例 :包括甲基’甲氧基’環己基(wHyl)。在本發明-些具體實施例中， 當R1為推電子基(例如甲基或苯基(phenyl)時），最大發光波長會發生藍位 移(blue Shift)。 "" 各^為相同或得且獨立為Η，G诚基心成氧基，^雜院基， 32°方曰基’ C㈣雜芳香基’或C3—2。環絲。較佳情況為，以推電， =ΓΓ °代細伽f基，異了基，何減。或者，_ γ =在-起而與其所連接之碳原子共_成4至14 M之芳香環或 衣。在本發明一些具體實施例中，兩個R2連接在一起而與其所連接之碳原曰 1260339 子共同形成一苯環(benzene ring)。4至14員之芳香環的其他具體例子包 括萘(naphthalene)和菲(phenanthrene)。另外，在本發明另一些具體實施 例中，此二個R2係個別不相連接歐。 、 各個R3為相同或不同，且獨立為H、CN、三氰乙婦基(tricyan〇vinyi)、 鹵素、CX3、C^8烷基、Cb烷氧基、G—8雜烷基、G-2。芳香基、C3_2。雜芳香基、 或Cm。環烷基，其中X為鹵素。較佳情況為，R3為拉電子基 (electron-withdrawing group)，例如鹵素、CN、三氰乙烯基，或 CL，其 中X為鹵素。適合之拉電子基包括F、⑶、⑶、和三氰乙烯基。在本發明 -些具體實施例中’當R3為拉電子基(如F)時，最大發光波長會產生藍位移。 母個R4為Η、Cl-成基、G-3院氧基或經4素(？、c卜Br)取代之Ci_3燒 · 基。 下列舉出域本發明之機金屬錯合物⑽定實例：
10 1260339
在上述化合物中，R2係為相同或不同之曱基、異丁基、或甲氧基。 本發明之有機金屬錯合物可發光，特別是在數個具體例子中是發綠色 兔光’或可做為綠色光摻入物(d〇pant)材料，可使用於例如的發光介 j中例如’使用於有機發光介質層的發光層中、或進一步於有機發光 枝層巾做鱗鱗卿衡料。此種發光 於綠光材料中較高發光效率者。 ㈣7蜀 實例 、下藉由數個，蝴以更進—步說明本㈣之特徵和優點。 實施例1 成 Iridium(III) bis[l，2-diphenylHenzoinTH 1 1 (tehHsUlyl) b〇me)(化合物 d,1 ㈣az〇le] (111)雙[1，2-二苯基η—苯并咪唑](四彳丨 合成途徑如下： 1260339
Λ
Ν-Ν Ν-Ν -» c2h5oc2h4oh Na2C〇3 reflux 〇-ν
A A
'N—N N—N < n_nwn_n 化合物⑴ 步驟 1 :將 N-phenyl-l，2-phenylenediamine (N-苯基 -1，2-苯二胺）（7.36g，40 _〇l) 40 ml 加入 250 ml 圓底瓶 後，加入三乙胺10 ml，冷卻至〇。〇。另取benzoyl chloride (苯 甲醯氯）（5· 6g，40 mmol)加入40 ml之二氯曱烷溶液後，再 緩慢注入250 ml圓底瓶，並在氮氣環境下反應6小時。反應 結束後加入乙醚後有沉澱析出。將固體產物過濾收集後，以乙 醚沖洗固體數次，最後將固體產物以減壓加熱方式，脫水後形 成最後產物：l，2-diphenyl-lH-benzoimidazole (1，2-二苯基 -1H-苯并咪唑），產率為7.56g，70°/〇。 步驟 2 :將 1，2-diphenyl-lH-benzoimidazole (6· 75 g，25 mmol)與 iridium(III)chloride trihydrate [氯化錶（III)三 12 1260339 水合物](4.2 g，12 mmol)加入250 ml圓底瓶後，加入6〇 ml ethy〇xyethan〇l (乙氧基乙醇）與2〇 ml水之混合溶液，在氮 氣下加熱迴流12小時，冷卻後有黃色沉澱物生成。以去離子 水與己烧（hexane)沖洗沉澱物數次，可得iridium dichloro-bridged dimer (氯化銥橋接之二聚物）（7· 35 g，4. 8 mmol) 〇 步驟 3 ··將上述 Iridium dichloro-bridged dimer (7· 35g， 4· 8 mmo 1)與四（1-啦哇）棚酸（s〇dium tetrakis(l-pyrazo 1 y 1) borate) (3.02 g，10 mmol)溶於乙氧基乙醇（ethoxyethanol) 中’並於室溫下反應12小時後，可得產物i r i d i um (111) bis[(l, 2-diphenyl )-1H-benzoimidazole] (tetrakis(l-pyrazolyl) borate) (5· 04g, 5mmol)(化合物 1)。最終產物係以連續昇華法加以純化之。 實施例2 合成 Iridium(III) bis[2-(2,4-difluoro-pheny1)-1-pheny1-1H- benzoimidazole] (tetrakis(l-pyrazolyl) borate)(化合物（2)) 銥（III)雙[2-(2, 4-二氟苯基H-苯基-1H-苯并咪唑](四（1-吡唑)硼酸）
化合物（2) 步驟 1 :將 N-phenyl-1, 2-phenylenediamine (1. 84 g，1〇 mmol)與40ml二氯甲烧加入250ml圓底瓶後，加入三乙胺3 13 1260339 ml ’ 冷伸至 〇c。另取 2,4-dif luoro-benzoy 1 chloride (2, 4- 二氟-苯曱醯氯）（1·94 g，Π mm〇l)加入ml之二氣甲烷 溶液後，再緩慢注入25〇 ml圓底瓶，並在氮氣環境下反應6 小時。反應結束後加入乙醚有沉澱析出，將固體產物過濾收集 後’以乙醚沖洗固體數次，最後將固體產物以減壓加熱方式， 脫水後 形成最 後產物 ： 2 (2,4-difluoro-phenyl)-l-pheny1-lH-benzoimidazole [2-(2, 4-一氟笨基）-1-苯基-1H-笨并u米嗤]，產率為1 · 83 g， 60%。 步驟 2 :將2-(2,4-以€111〇1'〇-01161171)-111161^1-111- benzoimidazole ( 1.83 g， 6 mmol)與 iridium(III)chloride trihydrate (1· 1 g，3 mmol)加入 250ml 圓底瓶後，加入 30ml 乙氧基乙醇與10 ml水之混合溶液，在氮氣下加熱迴流12小 時，冷卻後有黃色沉澱物生成。以去離子水與己烷沖洗沉殿物 數次，可得 Iridium dichloro-bridged dimer (2.01 g，1· 2 mmol) ° 步驟 3 :將上述 Iridium dichloro-bridged dimer (2. 01g， 1 · 2 mmo 1)與四（1-D比嗤）硼酸（sodium tetrakis(l-pyrazolyl) borate) (0.91g，3 mmol)溶於乙氧基乙醇（ethoxyethanol) 中，並於室溫下反應12小時後，可得產物iridium(III) bis[2-(2,4-di fluoro-phenyl)-1-pheny1-1H-benzoimidazol e] (tetrakis(l-pyrazolyl) borate) (l.〇8g，lmmol)(化合 物2)。最終產物係以連續昇華法加以純化之。 實施例3 合成 Iridium( III) bis[ 1, 2-dipheny 1-1 H-benzoimidazole] 14 1260339 (bis(l-pyrazolyl) borate) 銥（Π I)雙[1，2-二苯基-1H-苯并咪唑](二（1-吡唑）硼酸）
化合物（3) 如實施例1所述之合成步驟，但以sodium carbonate (lOmmol)及 pyrazole (lOmmol)取代 sodium tetrakis(l-pyrazolyl)borate 進行，得 到標題所稱之化合物。 實施例4 合成 Iridium(III) bis[2-(2,4-difluor〇-phenyl)-l-phenyl-lH- benzoimidazole] (bis(l-pyrazolyl) borate)
化合物（4) 錶(ΠΙ)雙[2-(2, 4_二氟苯基M-苯基-1H-苯并咪唑](二(1-Q比唑)） 如實施例2所述之合成步驟，但以sodium carbonate (3mmol)及 pyrazol(3mmol)取代 sodium tetrakisd-pyrazolyDborate 進行，得到標 題所稱之化合物。 15 l26〇339 第1圖顯示化合物（1)及（2)在不同波長下在CH2C12溶液中 測得之螢光光譜。對於化合物（1 )，在與咪唑環和I r連接之苯 %上，沒有取代基，所測得的最大發光波長為5丨5 。當苯環 在與咪唑環對位（para)及鄰位（meta)的位置上有 取代時（如化合物2)，會有藍位移發生，波長位移至删:。 雖然本發明已以較佳實施例揭露如上1其並非用以限定 + ¾明。任何熟習此技蓺者， 内，去可你此^ π者在不脫離本發明之精神和範圍 附之“專二更動與潤飾。因此本發明之保護範圍當視後 【圖式簡單說明】 H形^ 、化口物化合物⑴和(2)在不同波長下之光致發光(PL)強度的 16
Claims (1)
- 日期：95年3月24 0 「.· S i I26〇!?3?30362 1專利説明書修正本 十、申請專利範圍： 丄有枝至屬錯合物，其係為綠色碟光摻入物(d叩邱〇材料，具有下 列化學式(I)或(II):其中， Μ為一過渡金屬； 為Η鹵原子、Ci-18烧基、Ci_18烧氧基、C3_18雜烧基、C3_2G芳香基、 C3_2〇雜芳香基、或C3，環絲； 每個R1為Η ; 母们為相同或不同，且為Η、CN、三氰乙烯基(tricyanovinyl)、鹵 素、cx3、c148燒基、Ci_is烷氧基、c㈣雜烷基、c3_2G芳香基、c3_2G雜芳香 基、或c3_20環燒基，其中χ為函素；及 每個R為Ή、烷基、Q_3烷氧基、或經鹵素(F、a、Br)取代之CM 烷基。 ° 17 1 ·如申請專利範圍第1項所述之有機金屬錯合物，其中Μ為Ir、Pt、 Os、Re、Ru、或处。 12603氣6 21妻利説明書修正本 3.如申請專利範圍第1 日期：95年3月24 G 項所边之有機金屬錯合物，其具有下列化學式之其中，R2係為氫。 4·一種有機電致發卉奘μ廿a ， ,M 几衣且，其包括一對電極，以及在該對電極之間的一 有機發光介質層， /、 有柢^光;|貝層包括一有機金屬錯合物，作為綠色鱗光摻入物 (dopant)㈣’具有化學式(1)或⑼： 18 Θ斯：95年3月24日 ⑻ 其中， Μ為一過渡金屬； R1為Η、鹵原子、Cm8絲、Ci.i8烧氧基、c^雜烧基、c㈣芳香基、 Cy雜芳香基、或C㈣環烷基； 每個R2為Η ; 各每個R1相同或不同，且為H、CN、三氰乙___峨、齒 每個R4為H、c :CX3 q_18燒基、Ci，烧氧基、^雜炫基、c㈣芳香基、^雜 基、或Q-2。環院基，其中叉為南素；及 - 炫基。3燒基Ci·3燒氧基、或經鹵素(F、ci、Br)取代之q 3 5.如申請專利範圍第 〇s、Re、Ru、或处。 6·如申請專利範園第 合物具有下列化學式之_ 4項所述之有機電致發光裝置，其中Μ為Ir、pt、 4項所述之有機電致發光裝置，其中該有機金屬錯 19 A362號春利説明書修正本 Θ期：95年3月24 B其中，R2係為氫。 7.如申請專利範圍第4項所述之有機電致發光裝置，其中該有機發光介 質層包括一發光層，且該發光層包括如申請專利範圍第4項所述之有機金 屬錯合物。 20
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| JPWO2006008976A1 (ja) | 2004-07-16 | 2008-05-01 | コニカミノルタホールディングス株式会社 | 白色発光有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| JP2006054236A (ja) | 2004-08-10 | 2006-02-23 | Konica Minolta Holdings Inc | 有機エレクトロルミネッセンス素子、表示装置及び照明装置 |
| TWI260339B (en) * | 2004-10-07 | 2006-08-21 | Au Optronics Corp | Organometallic compound and organic electroluminescent device including the same |
-
2004
- 2004-10-07 TW TW093130362A patent/TWI260339B/zh active
-
2005
- 2005-01-28 US US11/045,995 patent/US7601437B2/en active Active
- 2005-09-30 JP JP2005286102A patent/JP4448482B2/ja active Active
-
2009
- 2009-06-30 JP JP2009155421A patent/JP5186442B2/ja active Active
Also Published As
| Publication number | Publication date |
|---|---|
| US7601437B2 (en) | 2009-10-13 |
| JP2009263383A (ja) | 2009-11-12 |
| JP5186442B2 (ja) | 2013-04-17 |
| US20060078758A1 (en) | 2006-04-13 |
| JP2006117660A (ja) | 2006-05-11 |
| JP4448482B2 (ja) | 2010-04-07 |
| TW200611958A (en) | 2006-04-16 |
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