CN104628787A - 一种绿光发射铱磷光配合物及其制备方法 - Google Patents
一种绿光发射铱磷光配合物及其制备方法 Download PDFInfo
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 22
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 20
- 238000002360 preparation method Methods 0.000 title abstract description 6
- 238000010668 complexation reaction Methods 0.000 title 1
- 239000003446 ligand Substances 0.000 claims abstract description 8
- LFIPLQWBFZMHQX-UHFFFAOYSA-N 2-(4-phenylphenyl)pyridine Chemical compound C1=CC=CC=C1C1=CC=C(C=2N=CC=CC=2)C=C1 LFIPLQWBFZMHQX-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052751 metal Inorganic materials 0.000 claims description 9
- 239000002184 metal Substances 0.000 claims description 9
- 125000004122 cyclic group Chemical group 0.000 claims description 8
- 239000000126 substance Substances 0.000 claims description 4
- 238000010189 synthetic method Methods 0.000 claims description 3
- 239000000539 dimer Substances 0.000 abstract description 4
- 239000002994 raw material Substances 0.000 abstract description 2
- DANYXEHCMQHDNX-UHFFFAOYSA-K trichloroiridium Chemical compound Cl[Ir](Cl)Cl DANYXEHCMQHDNX-UHFFFAOYSA-K 0.000 abstract description 2
- MJRFDVWKTFJAPF-UHFFFAOYSA-K trichloroiridium;hydrate Chemical compound O.Cl[Ir](Cl)Cl MJRFDVWKTFJAPF-UHFFFAOYSA-K 0.000 abstract 1
- 239000000463 material Substances 0.000 description 8
- 238000001228 spectrum Methods 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 229910052799 carbon Inorganic materials 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 239000012065 filter cake Substances 0.000 description 2
- 238000004128 high performance liquid chromatography Methods 0.000 description 2
- 238000001819 mass spectrum Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 238000000103 photoluminescence spectrum Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229910021638 Iridium(III) chloride Inorganic materials 0.000 description 1
- -1 Jaemin Lee Chemical class 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001793 charged compounds Chemical class 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000005594 diketone group Chemical group 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 150000002503 iridium Chemical class 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 230000004001 molecular interaction Effects 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 238000006884 silylation reaction Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 238000000967 suction filtration Methods 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
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- 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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- 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
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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
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/18—Metal complexes
- C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
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Abstract
本发明公开了一种绿光发射铱磷光配合物及其制备方法,这种铱磷光配合物以2-(联苯基)吡啶为环金属配体，2,2,6,6-四甲基-3,5-庚二酮(tmd)为辅助配体，Ir(bppy)2(tmd)]，其最大发射波长在533nm，为典型的绿光发射。以水合三氯化铱为原料，合成铱氯桥二聚体(dppy)2Ir2Cl2(dppy)2，再和tmd在碱性条件下反应制备得到[Ir(bppy)2(tmd)]，产率达85％，纯度高达99.5％。其化学结构式为：
Description
技术领域
本发明涉及有机发光二极管(OLED)用电致磷光材料合成技术领域，具体是绿光发射铱磷光配合物及其制备方法。
背景技术
OLED具有对比度高、超薄、视角广、能耗低、响应速度快、色彩绚丽、柔性等特征，被视为最新一代的“绿色节能”显示技术和最具竞争潜力的新一代固态光源。
发光材料是OLED的核心关键材料之一，它的发光性能直接决定着OLED器件的性能。在OLED的发展中，将磷光配合物作为发光材料引入到OLED的发光层，使器件的最大内量子效率由原来荧光材料的25％提高到磷光材料的100％，从理论上将OLED的最大效率提高了三倍，从而开辟了磷光OLED研究的新领域。磷光材料主要是一些重金属(如铱、铂、钌、锇、铜等)的配合物，到目前为止，在诸多磷光材料中，基于铱(Ir)配合物发光的磷光OLED具有最高的发光效率，部分小分子铱磷光配合物已商业化，并成功应用于OLED中。
结构式1：基于2-(联苯基)吡啶及其衍生物环金属配体的铱磷光配合物
Jaemin Lee等(Synthetic Metals,2012,162:1961-1967)报道了以2-(联苯基)吡啶及其衍生物环金属配体的铱磷光配合物(结构式1)，通过在环金属配体的吡啶环上引入硅烷基，能够改善铱磷光配合物的溶解性，减小分子间相互作用，从而提高器件效率。通过改变环金属配体和辅助配体的结构，均能调控铱磷光配合物的最大发射波长和发光效率，目前的研究主要集中在环金属配体的结构修饰，尚未见基于2,2,6,6-四甲基更二酮为辅助配体的这类铱磷光配合物的报道。
鉴于此，本发明提供了一种以2-(联苯基)吡啶为环金属配体，2,2,6,6-四甲基-3，5-庚二酮为辅助配体的绿光发射铱磷光配合物及其合成方法，为OLED提供一种发光体的选择。
发明内容
本发明的目的是提供一种绿光发射的铱磷光配合物及其制备方法，这种铱磷光配合物以2-(联苯基)吡啶为环金属配体，2,2,6,6-四甲基庚二酮为辅助配体，2,2,6,6-四甲基-3,5-庚二酮为辅助配体，化学式为Ir(bppy)2(tmd)，其结构式如下为：
本发明的铱磷光配合物为典型的绿光发射，最大发射波长在533nm，Ir(bppy)2(tmd)的光致发光光谱如图1。其合成方法是以水合三氯化铱为原料制备得到铱的氯桥二聚体，再和2,2,6,6-四甲基-3,5-庚二酮反应，过滤得到粗品，然后通过硅胶柱分离得到纯品。其化学反应路线为：
本发明的特征在于获得了一种全新的绿光发射的铱磷光配合物及其制备方法，为OLED提供一种发光体的选择。
附图说明
图1为本发明的Ir(bppy)2(tmd)的光致发光光谱。图2为Ir(bppy)2(tmd)的高效液相色谱(HPLC)图。图3为Ir(bppy)2(tmd)的氢谱。图4Ir(bppy)2(tmd)的碳谱。图5Ir(bppy)2(tmd)的质谱。
具体实施方式
(1)二聚体(dppy)2Ir2Cl2(dppy)2的合成
在500mL的圆底烧瓶中加入16.33g(70.7mmol)dppy，溶解在120mL乙二醇单乙醚中，之后加入9.96g(28.3mmol)三氯化铱和80mL去离子水，反复充放N2三次后，N2气氛下120℃加热回流24h，混合物冷却至室温。过滤，滤饼分别用30mL丙酮，40×2mL水，30×2mL丙酮洗涤，真空干燥，得到的粗产品17.3克，直接用于下一步反应。
(2)配合物Ir(dppy)2(tmd)的合成
将8.38g(6.09mmol)铱氯桥二聚体(dppy)2Ir2Cl2(dppy)2加入到250mL三口瓶中，加入3.23g(30.5mmol)无水Na2CO3和210mL乙二醇单乙醚，并加入5.6g(30.4mmol)2,2,6,6-四甲基-3,5-庚二酮，反复充放N2三次后，N2气氛下135℃加热回流24h，混合物冷却至室温后倒入大量水中，抽滤，滤饼烘干后用二氯甲烷溶解，快速过柱，除去溶剂后剩余物用二氯甲烷和甲醇混合液重结晶得黄色固体产物7.8克，产率约为86.4％，产品纯度99.83％(HPLC，图2)。
结构解析：
(1)元素分析，理论值(％)：C 64.64，N 3.35H 5.14；实测值(％)：C 64.61N 3.34H 5.12。实测值和理论值相吻合。
(2)氢谱(1H NMR，400MHz，CDCl3，图3)，化学位移(ppm)：8.45(d，2H)，7.94(d，2H)，7.79(t，4H)，7.58(t，4H)，7.37(t，6H)，7.06(d，2H)，6.98(d，2H)，6.50(d，2H)，5.51(s，1H)，0.92(s，18H)。
(3)碳谱(13C NMR，400MHz，CDCl3，图4)，化学位移(ppm)：194.45,168.55，149.28,148.24,145.42,142.19,136.61,133.89,133.09,128.53,127.68,126.41,125.96,122.10,121.18,117.99,89.49,41.13,28.12。
(4)质谱(ESI-MS，图5)：出现了836分子离子峰，与Ir(bppy)2(tmd)的分子量相吻合。
元素分析、氢谱、碳谱和质谱的结果表明，样品与Ir(bppy)2(tmd)目标化合物相吻合。
Claims (3)
1.一种铱磷光配合物，特征在于：结构式如下，以2-(联苯基)吡啶为环金属配体，2,2,6,6-四甲基-3,5-庚二酮为辅助配体，化学式为Ir(bppy)2(tmd)，结构式为：
2.如权利要求1中的铱磷光配合物，其特征在于：为典型的绿光发射，最大发射波长在533nm。
3.如权利要求1或2中的铱磷光配合物，其合成方法及路线如下：
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN105949244A (zh) * | 2016-05-25 | 2016-09-21 | 昆明贵金属研究所 | 两种绿光铱磷光配合物及其合成方法 |
| CN106243155A (zh) * | 2016-08-05 | 2016-12-21 | 昆明贵金属研究所 | 一类铱磷光材料及其制备方法 |
| CN108808449A (zh) * | 2018-06-22 | 2018-11-13 | 南京邮电大学 | 一种基于三线态激子放大器的有机激光薄膜器件及应用 |
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| CN105949244A (zh) * | 2016-05-25 | 2016-09-21 | 昆明贵金属研究所 | 两种绿光铱磷光配合物及其合成方法 |
| CN106243155A (zh) * | 2016-08-05 | 2016-12-21 | 昆明贵金属研究所 | 一类铱磷光材料及其制备方法 |
| CN108808449A (zh) * | 2018-06-22 | 2018-11-13 | 南京邮电大学 | 一种基于三线态激子放大器的有机激光薄膜器件及应用 |
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