CN102558247A - 4-膦基-1,5-萘啶衍生物铜(i)配合物发光材料和应用 - Google Patents
4-膦基-1,5-萘啶衍生物铜(i)配合物发光材料和应用 Download PDFInfo
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- VMQMZMRVKUZKQL-UHFFFAOYSA-N Cu+ Chemical compound [Cu+] VMQMZMRVKUZKQL-UHFFFAOYSA-N 0.000 title claims abstract description 17
- DYVRKNASEITMNK-UHFFFAOYSA-N 1,5-naphthyridin-4-ylphosphane Chemical class PC1=CC=NC2=CC=CN=C12 DYVRKNASEITMNK-UHFFFAOYSA-N 0.000 title claims abstract description 4
- 239000000463 material Substances 0.000 title abstract description 8
- 239000003446 ligand Substances 0.000 claims abstract description 9
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 150000002500 ions Chemical class 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 3
- -1 hexafluoro-phosphate radical Chemical class 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-M perchlorate Inorganic materials [O-]Cl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-M 0.000 claims description 2
- VLTRZXGMWDSKGL-UHFFFAOYSA-N perchloric acid Chemical compound OCl(=O)(=O)=O VLTRZXGMWDSKGL-UHFFFAOYSA-N 0.000 claims description 2
- RPGWZZNNEUHDAQ-UHFFFAOYSA-N phenylphosphine Chemical compound PC1=CC=CC=C1 RPGWZZNNEUHDAQ-UHFFFAOYSA-N 0.000 claims description 2
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 2
- 150000005055 1,5-naphthyridines Chemical class 0.000 claims 1
- VMLKTERJLVWEJJ-UHFFFAOYSA-N 1,5-naphthyridine Chemical compound C1=CC=NC2=CC=CN=C21 VMLKTERJLVWEJJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000005540 biological transmission Effects 0.000 abstract 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 239000010949 copper Substances 0.000 description 29
- 239000013078 crystal Substances 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- 238000003756 stirring Methods 0.000 description 10
- RYXZOQOZERSHHQ-UHFFFAOYSA-N [2-(2-diphenylphosphanylphenoxy)phenyl]-diphenylphosphane Chemical compound C=1C=CC=C(P(C=2C=CC=CC=2)C=2C=CC=CC=2)C=1OC1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RYXZOQOZERSHHQ-UHFFFAOYSA-N 0.000 description 9
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 238000001914 filtration Methods 0.000 description 6
- 238000001953 recrystallisation Methods 0.000 description 6
- 125000006850 spacer group Chemical group 0.000 description 6
- 150000001875 compounds Chemical class 0.000 description 5
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 244000124209 Crocus sativus Species 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 102100029290 Transthyretin Human genes 0.000 description 2
- 108050000089 Transthyretin Proteins 0.000 description 2
- 238000002484 cyclic voltammetry Methods 0.000 description 2
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
- VURFVHCLMJOLKN-UHFFFAOYSA-N diphosphane Chemical compound PP VURFVHCLMJOLKN-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- STCOOQWBFONSKY-UHFFFAOYSA-N tributyl phosphate Chemical compound CCCCOP(=O)(OCCCC)OCCCC STCOOQWBFONSKY-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 238000004847 absorption spectroscopy Methods 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 150000004699 copper complex Chemical class 0.000 description 1
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 description 1
- 229910000071 diazene Inorganic materials 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000005518 electrochemistry Effects 0.000 description 1
- 238000005401 electroluminescence Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000005284 excitation Effects 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 150000005054 naphthyridines Chemical class 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 150000003248 quinolines Chemical class 0.000 description 1
- 125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
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Abstract
本发明提供一种4-膦基-1,5-萘啶衍生物铜(I)配合物发光材料和应用。该类铜(I)配合物首次将1,5-萘啶引入到不对称的N^P配体中,相较典型的8-膦基喹啉铜(I)配合物有着较低的光化学能隙和电化学能隙。该类配合物可作为有机发光二极管的发光层或电子传输层。
Description
技术领域
本发明属于光电材料技术领域。具体涉及一种4-膦基-1,5-萘啶衍生物铜(I)配合物发光材料和应用。所述化合物具有发光性能,可以作为有机发光二极管的发光层或电子传输层。
技术背景
近年来,随着有机发光二极管器件(Organic Light-emitting diodes,OLEDs)在薄膜显示和照明等高新技术领域的广泛应用,人们对有机发光材料的设计和选择提出了更高的要求。铜(I)配合物发光材料由于具有价格低廉、环境友好等特点而成为目前有机电致发光领域的热点(Annu.Rep.Prog.Chem.,Sect.A,2010,106,526.)。
为了提高铜(I)配合物发光材料的发光性能,人们对其进行了大量研究。早在1999年,吉林大学的马於光课题组就将铜(I)配合物运用到OLED领域,合成了一个多核的一价铜配合物Cu4(图1),但他们在研究中发现,铜一价化合物的电荷转移激发态产生的发射信号普遍比较弱,并且寿命较短(Adv.Mater,1999,11,852.)。
图1Cu4的分子结构
2002年由McMillin课题组采用2,9位烷基取代的1,10-菲啰啉和醚键偶联的三苯基膦作为配体合成得到[Cu(dmp)(DPEphos)]+配合物,他们发现引入多齿的含磷配体可抑制激基复合物的产生,能够有效的避免溶剂淬灭作用,该配合物在溶液中的荧光效率达到了16%(J.Am.Chem.Soc.,2002,124,6.)。
图2[Cu(dmp)(DPEphos)]BF4的分子结构
2009年,卢灿忠等引入了不对称的N^P配体,合成得到如图3所示铜(I)配合物(Dalton Trans.,2009,9388.),表明该类含有不对称N^P配体的铜(I)配合物比含有对称的二亚胺配体或者二膦配体的化合物具有较高的还原态和较稳定的激发态。
图3[Cu(N^P)(POP)]BF4的分子结构
总之,目前基于喹啉的不对称N^P配体被广泛应用于Cu(I),Ni(I),Ru(II)和Pd(II)等金属配合物的合成(J.Organomet.Chem.,1997,535,183;Inorg.Chem.,2003,42,785.),而基于萘啶的不对称N^P配体的金属配合物却未见报道。并且萘啶类化合物与喹啉类化合物相比,其半波还原电位相对较高,应为更理想的研究对象(Chem.Lett.,1993,10,1775.)。为此,本发明设计合成了带有不同取代基的不对称的N^P配体4-膦基-1,5-萘啶,进而合成得到其铜(I)配合物,提高其铜(I)配合物的半波还原电位,使得该类化合物共轭体系增强,轨道能隙降低,以期制备出长寿命的铜(I)配合物电致发光器件。
发明内容
本发明的目的在于提出一类具有优良的电子传输能力和发光性能的、含有不同取代基的4-膦基-1,5-萘啶铜(I)配合物以及其作为有机发光二极管的发光层的应用。
本发明设计的这类以4-膦基-1,5-萘啶衍生物为配体的铜(I)配合物的发光机理是基于MLCT。量化计算结果表明,在喹啉配体中引入富含电子的氮原子,可以增加该类杂环分子的半波还原电位,使得该类化合物共轭体系增强,轨道能隙降低。实验结果表明,以4-膦基-1,5-萘啶衍生物为配体的铜(I)配合物的光化学能隙和电化学能隙显著降低。
本发明设计并合成了一系列以4-膦基-1,5-萘啶衍生物为配体的铜(I)配合物,该配合物具有如下I或II所示的结构:
其中,R1选自氢、甲基、苯基;R2选自氢、甲基、苯基;R3选自苯基、苄基、C1-C8的烷基。
前述结构通式中P^P代表两个单独的三苯基膦配体或桥联的苯基膦双齿配体,选自以下配体中的任意一组:
前述结构通式中X-代表抗衡负离子,优选自六氟磷酸根、四氟硼酸跟、高氯酸根等。
P^P及抗衡离子X-可与4-膦基-1,5-萘啶类配体任意组合。
前述配合物的结构通式中,R1优选为氢;R2优选为氢;R3优选为苯基。
前述配合物的结构通式中,R1优选为甲基;R2优选为氢;R3优选为苯基。
前述配合物的结构通式中,P^P优选配体1。
前述配合物的结构通式中,P^P优选配体3。
所有Cu(I)配合物具有室温荧光发射性质,可作为发光材料用于制备有机电致发光器件。
附图说明
图1给出了实例中配合物(1-6)的单晶结构。
图2给出了实例中配合物(1-6)二氯甲烷溶液中的紫外可见吸收光谱(c=5.0×10-5molL-1)。
图3给出了实例中配合物1-6的固体荧光发射光谱(λmax=375nm)。
图4给出了实例中配合物1和2与已知配合物[Cu(QN)2](PF6)在乙腈溶液中的循环伏安曲线,电解质为0.1mol/V的TBPA溶液,工作电极为Pt电极,扫描速率为100mV/S。
图5给出了实例中配合物3-6与经典配合物[Cu(QN)(PPh3)2](PF6)和[Cu(QN)(DPEphos)](PF6)在乙腈溶液中的循环伏安曲线,电解质为0.1mol/V的TBPA溶液,工作电极为Pt电极,扫描速率为100mV/S,以二茂铁为内标。
具体实施方式
实施例1:[Cu(ND)2](PF6)(1)的合成
氩气保护条件下,将含有ND(0.41g,1.3mmol)的10mL CH2Cl2溶液缓慢加入到含[Cu(NCCH3)4](PF6)(0.24g,0.65mmol)的30mL甲醇溶液中,室温搅拌2h后过滤,滤液真空除溶剂得红色固体。固体用乙醚洗涤,四氢呋喃/甲醇/乙醚(2∶1∶6v/v/v)重结晶,得到红色晶体[Cu(ND)2](PF6)0.85g,产率78%。该配合物的晶体结构通过X射线单晶衍射仪确定,其晶体学参数为:空间群P21/C,a=14.386(3),b=23.133(5),c=23.326(5),α=90.00,β=105.24(3),γ=90.00°,
实施例2:[Cu(mND)2](PF6)(2)的合成
氩气保护条件下,将含有mND(0.33g,1.0mmol)的10mlCH2Cl2溶液缓慢加入到含[Cu(NCCH3)4](PF6)(0.19g,0.5mmol)的30mL甲醇溶液中,室温搅拌2h后过滤,滤液真空除溶剂得橘黄色固体。固体用乙醚洗涤,四氢呋喃/甲醇/乙醚(2∶1∶6v/v/v)重结晶,得到橘黄色晶体[Cu(mND)2](PF6)0.59g,产率62%。该配合物的晶体结构通过X射线单晶衍射仪确定,其晶体学参数为:空间群C2/C,a=16.242(3),b=17.274(4),c=17.517(4),α=90.00,β=117.20(3),γ=90.00°,
实施例3:[Cu(ND)(PPh3)2](PF6)(3)的合成
氩气保护条件下,将含有ND(0.55g,1.75mmol)的15mlCH2Cl2溶液缓慢加入到含[Cu(NCCH3)4](PF6)(0.65g,1.75mmol)的35mL甲醇溶液中,室温搅拌1h后再加入含三苯基磷(PPh3)(0.92g,3.5mmol)的15mlCH2Cl2溶液,室温搅拌1h后过滤,滤液真空除溶剂得黄色固体。固体用乙醚洗涤,四氢呋喃/甲醇/乙醚(2∶1∶6v/v/v)重结晶,得到黄色晶体[Cu(ND)(PPh3)2](PF6)1.51g,产率82.3%。该配合物的晶体结构通过X射线单晶衍射仪确定,其晶体学参数为:空间群P21/c,a=12.520(3),b=16.408(3),c=26.583(5),α=90.00,β=93.58(3),γ=90.00°,
实施例4:[Cu(mND)(PPh3)2](PF6)(4)的合成
氩气保护条件下,将含有mND(0.55g,1.75mmol)的15mlCH2Cl2溶液缓慢加入到含[Cu(NCCH3)4](PF6)(0.65g,1.75mmol)的35mL甲醇溶液中,室温搅拌1h后再加入含三苯基磷(PPh3)(0.92g,3.5mmol)的15mlCH2Cl2溶液,室温搅拌1h后过滤,滤液真空除溶剂得黄色固体。固体用乙醚洗涤,四氢呋喃/甲醇/乙醚(2∶1∶6v/v/v)重结晶,得到黄色晶体[Cu(mND)(PPh3)2](PF6)1.41g,产率75.8%。该配合物的晶体结构通过X射线单晶衍射仪确定,其晶体学参数为:空间群P21/N,a=11.681(2),b=23.919(5),c=19.959(4),α=90.00,β=95.94(3),γ=90.00°,
实施例5:[Cu(ND)(DPEphos)](PF6)(5)的合成
氩气保护条件下,将含有ND(0.33g,1.0mmol)的10mlCH2Cl2溶液缓慢加入到含[Cu(NCCH3)4](PF6)(0.38g,1.0mmol)的20mL甲醇溶液中,室温搅拌1h后再加入含二(2-二苯基膦)苯基醚(DPEphos)(0.55g,1.0mmol)的10mlCH2Cl2溶液,室温搅拌1h后过滤,滤液真空除溶剂得黄色固体。固体用乙醚洗涤,四氢呋喃/甲醇/乙醚(2∶1∶6v/v/v)重结晶,得到黄色晶体[Cu(ND)(DPEphos)](PF6)0.75g,产率70.7%。该配合物的晶体结构通过X射线单晶衍射仪确定,其晶体学参数为:空间群P21/C,a=10.446(2),b=27.349(6),c=17.882(4),α=90.00,β=99.86(3),γ=90.00°,
实施例6:[Cu(mND)(DPEphos)](PF6)(6)的合成
氩气保护条件下,将含有mND(0.32g,1.0mmol)的10mlCH2Cl2溶液缓慢加入到含[Cu(NCCH3)4](PF6)(0.38g,1.0mmol)的20mL甲醇溶液中,室温搅拌1h后再加入含二(2-二苯基膦)苯基醚(DPEphos)(0.55g,1.0mmol)的10mlCH2Cl2溶液,室温搅拌1h后过滤,滤液真空除溶剂得黄色固体。固体用乙醚洗涤,四氢呋喃/甲醇/乙醚(2∶1∶6v/v/v)重结晶,得到黄色晶体[Cu(mND)(DPEphos)](PF6)0.80g,产率74.4%。该配合物的晶体结构通过X射线单晶衍射仪确定,其晶体学参数为:空间群P21/C,a=10.545(2),b=27.969(6),c=17.994(4),α=90.00,β=101.28(3),γ=90.00°,
虽然已经用优选实施例详述了本发明,然而其并非用于限定本发明。任何本领域的技术人员,在不脱离本发明的精神和范围的情况下,应当可以作出各种修改与变更。因此本发明的保护范围应当视为所附的权力要求书所限定的范围。
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CN103570761A (zh) * | 2013-08-28 | 2014-02-12 | 渤海大学 | 一种对氧气敏感的铜配合物/复合发光材料及其制备方法以及在氧气传感器件上的应用 |
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Cited By (7)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103130841A (zh) * | 2013-03-25 | 2013-06-05 | 南京工业大学 | 一种5-(萘啶-4-基)三氮唑衍生物过渡金属配合物与发光应用 |
CN103570761A (zh) * | 2013-08-28 | 2014-02-12 | 渤海大学 | 一种对氧气敏感的铜配合物/复合发光材料及其制备方法以及在氧气传感器件上的应用 |
CN103570761B (zh) * | 2013-08-28 | 2016-05-25 | 渤海大学 | 一种对氧气敏感的铜配合物/复合发光材料及其制备方法以及在氧气传感器件上的应用 |
CN103833777A (zh) * | 2014-03-20 | 2014-06-04 | 中国计量学院 | 一种基于苯并噁唑基喹啉配体的亚铜配合物发光材料 |
US9741941B2 (en) | 2014-04-29 | 2017-08-22 | Universal Display Corporation | Organic electroluminescent materials and devices |
CN104099086A (zh) * | 2014-07-14 | 2014-10-15 | 中国计量学院 | 一种苯并噁唑基喹啉亚铜配合物发光材料的新晶型及其制备方法 |
CN104099086B (zh) * | 2014-07-14 | 2016-01-20 | 中国计量学院 | 一种苯并噁唑基喹啉亚铜配合物发光材料的新晶型及其制备方法 |
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