CN105732724A - 铱配合物及其制备方法和应用铱配合物的电致发光器件 - Google Patents
铱配合物及其制备方法和应用铱配合物的电致发光器件 Download PDFInfo
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- CN105732724A CN105732724A CN201610213735.1A CN201610213735A CN105732724A CN 105732724 A CN105732724 A CN 105732724A CN 201610213735 A CN201610213735 A CN 201610213735A CN 105732724 A CN105732724 A CN 105732724A
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- bis
- pyridine
- iridium
- trifluoromethyl
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- 229910052741 iridium Inorganic materials 0.000 title claims abstract description 55
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 title claims abstract description 54
- 238000002360 preparation method Methods 0.000 title claims description 12
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 claims abstract description 30
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims abstract description 25
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims abstract description 17
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 claims abstract description 15
- 239000003446 ligand Substances 0.000 claims abstract description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims abstract description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 10
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims abstract description 8
- 150000003918 triazines Chemical class 0.000 claims abstract description 7
- 239000000463 material Substances 0.000 claims description 25
- 150000001875 compounds Chemical class 0.000 claims description 18
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 claims description 16
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 15
- 150000003222 pyridines Chemical class 0.000 claims description 14
- 150000003230 pyrimidines Chemical class 0.000 claims description 13
- 125000003373 pyrazinyl group Chemical group 0.000 claims description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
- -1 pyrimidine radicals Chemical class 0.000 claims description 9
- 229910000029 sodium carbonate Inorganic materials 0.000 claims description 8
- 125000001424 substituent group Chemical group 0.000 claims description 8
- 238000006471 dimerization reaction Methods 0.000 claims description 7
- 230000005540 biological transmission Effects 0.000 claims description 6
- 230000027756 respiratory electron transport chain Effects 0.000 claims description 6
- 239000000758 substrate Substances 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 238000004440 column chromatography Methods 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- CINYXYWQPZSTOT-UHFFFAOYSA-N 3-[3-[3,5-bis(3-pyridin-3-ylphenyl)phenyl]phenyl]pyridine Chemical compound C1=CN=CC(C=2C=C(C=CC=2)C=2C=C(C=C(C=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)C=2C=C(C=CC=2)C=2C=NC=CC=2)=C1 CINYXYWQPZSTOT-UHFFFAOYSA-N 0.000 claims description 3
- ZOKIJILZFXPFTO-UHFFFAOYSA-N 4-methyl-n-[4-[1-[4-(4-methyl-n-(4-methylphenyl)anilino)phenyl]cyclohexyl]phenyl]-n-(4-methylphenyl)aniline Chemical compound C1=CC(C)=CC=C1N(C=1C=CC(=CC=1)C1(CCCCC1)C=1C=CC(=CC=1)N(C=1C=CC(C)=CC=1)C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 ZOKIJILZFXPFTO-UHFFFAOYSA-N 0.000 claims description 3
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 239000012141 concentrate Substances 0.000 claims description 3
- 239000012043 crude product Substances 0.000 claims description 3
- 230000006837 decompression Effects 0.000 claims description 3
- 239000000284 extract Substances 0.000 claims description 3
- 239000011521 glass Substances 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- 229910052738 indium Inorganic materials 0.000 claims description 3
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical group [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 230000004044 response Effects 0.000 claims description 3
- 238000000926 separation method Methods 0.000 claims description 3
- 239000002904 solvent Substances 0.000 claims description 3
- NZFDZFJVWFDFQV-UHFFFAOYSA-N 2,4-bis(trifluoromethyl)pyridine Chemical compound FC(F)(F)C1=CC=NC(C(F)(F)F)=C1 NZFDZFJVWFDFQV-UHFFFAOYSA-N 0.000 claims description 2
- 238000004821 distillation Methods 0.000 claims description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 238000002156 mixing Methods 0.000 claims description 2
- 239000000126 substance Substances 0.000 abstract description 5
- 238000000746 purification Methods 0.000 abstract description 3
- 238000000859 sublimation Methods 0.000 abstract description 3
- 230000008022 sublimation Effects 0.000 abstract description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 abstract 2
- 150000002503 iridium Chemical class 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 16
- 238000005401 electroluminescence Methods 0.000 description 14
- 238000001704 evaporation Methods 0.000 description 6
- 238000013461 design Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 241001597008 Nomeidae Species 0.000 description 3
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 3
- 239000004327 boric acid Substances 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000005525 hole transport Effects 0.000 description 3
- IMRWILPUOVGIMU-UHFFFAOYSA-N 2-bromopyridine Chemical compound BrC1=CC=CC=N1 IMRWILPUOVGIMU-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004020 luminiscence type Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000012044 organic layer Substances 0.000 description 2
- 230000005622 photoelectricity Effects 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- RSSDWSPWORHGIE-UHFFFAOYSA-N $l^{1}-phosphanylbenzene Chemical compound [P]C1=CC=CC=C1 RSSDWSPWORHGIE-UHFFFAOYSA-N 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WGFCNCNTGOFBBF-UHFFFAOYSA-N 2-bromopyrazine Chemical compound BrC1=CN=CC=N1 WGFCNCNTGOFBBF-UHFFFAOYSA-N 0.000 description 1
- PGFIHORVILKHIA-UHFFFAOYSA-N 2-bromopyrimidine Chemical compound BrC1=NC=CC=N1 PGFIHORVILKHIA-UHFFFAOYSA-N 0.000 description 1
- 208000019901 Anxiety disease Diseases 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- 239000010405 anode material Substances 0.000 description 1
- 230000036506 anxiety Effects 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 230000005311 nuclear magnetism Effects 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- QPUMEZIFDXYGPG-UHFFFAOYSA-N piperazine 1H-pyrrole Chemical compound N1CCNCC1.N1C=CC=C1 QPUMEZIFDXYGPG-UHFFFAOYSA-N 0.000 description 1
- 125000003386 piperidinyl group Chemical group 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 150000003921 pyrrolotriazines Chemical class 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
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Abstract
本发明涉及一类具有新型主配体、以2(5苯基1,3,4恶二唑2)苯酚为辅助配体的铱配合物,该系列铱配合物分子中的主配体是2(4,6二三氟甲基吡啶3)基吡啶、2(4,6二三氟甲基吡啶4)基吡啶、2(4,6二三氟甲基吡啶3)基嘧啶、2(4,6二三氟甲基吡啶4)基嘧啶、2(4,6二三氟甲基吡啶3)基吡嗪、2(4,6二三氟甲基吡啶4)基吡嗪和2(4,6二三氟甲基吡啶3)基三嗪、2(4,6二三氟甲基吡啶4)基三嗪衍生物。该发明涵盖的这类新型铱配合物不仅具有发光效率高、电子迁移率高、化学性质稳定、易升华提纯等优点以外,且器件性能优良。
Description
【技术领域】
本发明涉及有机电致发光器件技术领域,尤其涉及一类铱配合物及其制备方法和应用所述铱配合物的电致发光器件。
【背景技术】
在全球能源需求日益增长及生态环境堪忧的大背景下,各国政府相继大力发展基于高科技的可持续节能技术和产业。有机电致发光器件(OLEDs)因其视角广、亮度高、能耗低并可制备柔性器件等诸多优点,而倍受关注,被称为将主宰未来显示世界的关键技术。近年来,大量研究表明,在众多重金属元素配合物中,铱配合物被认为是OLEDs磷光材料的最理想选择。具有5d7 6s2外层电子结构的铱原子在形成+3价阳离子后,具有5d6电子组态,具有稳定的六配位八面体结构,使材料具有较高的化学稳定性和热稳定性。同时,Ir(III)具有较大的自旋轨道偶合常数(ξ=3909cm-1),有利于提高配合物的内量子产量并降低发光寿命,从而提高发光器件的整体性能。
作为磷光材料,铱配合物一般具有微秒级的,容易造成铱配合物的三重态-三重态以及三重态-激化子之间的磷光淬灭。另外,在目前的常用的材料中,空穴传输材料的空穴迁移率远高于电子传输材料的电子迁移率,而常用的主体材料也以空穴传输为主,这会导致大量多余的空穴在发光层和电子传输层界面的聚集。这些因素都会导致效率的降低和严重的效率滚降。研究表明,如果铱配合物具有较高的电子传输能力,能够有效的增加电子在发光层的传输和分布、拓宽电子-空穴的区域、平衡电子-空穴对的数量,极大的提高器件的效率,降低效率的滚降。
因此,有必要提供一种同时具有高发光效率和电子迁移率的铱配合物。
【发明内容】
本发明的目的在于提供一类含有新型主配体和2-(5-苯基-1,3,4-恶二唑-2-)苯酚辅助配体的绿光铱配合物及其制备方法,制备的高效磷光铱配合物可作为发光中心,应用于有机电致发光器件中。
本发明提供一种铱配合物,其含有两个主配体和一个2-(5-苯基-1,3,4-恶二唑-2-)苯酚辅助配体,所述主配体为2-(4,6-二三氟甲基吡啶-3-)基吡啶、2-(4,6-二三氟甲基吡啶-4-)基吡啶、2-(4,6-二三氟甲基吡啶-3-)基嘧啶、2-(4,6-二三氟甲基吡啶-4-)基嘧啶、2-(4,6-二三氟甲基吡啶-3-)基吡嗪、2-(4,6-二三氟甲基吡啶-4-)基吡嗪和2-(4,6-二三氟甲基吡啶-3-)基三嗪、2-(4,6-二三氟甲基吡啶-4-)基三嗪衍生物中的任意一种,所述主配体中,和铱以C原子配位的吡啶衍生物为:所述吡啶衍生物和不同主配体中的吡啶基、嘧啶基、吡嗪基和三嗪基的连接位置不同;所述吡啶基、嘧啶基、吡嗪基和三嗪基的任意位被卤素或烷基取代,所述吡啶基上取代基的数量为0-4,所述嘧啶基和吡嗪基上取代基的数量为0-3,所述三嗪基上取代基的数量为0-2。
优选的,所述卤素为F,所述烷基为三氟甲基、甲基中的任意一种。
优选的,所述主配中的4,6-二三氟甲基吡啶在不同主配体中和吡啶基、嘧啶基、吡嗪基和三嗪基连接的位置不同,取自3位和4位;所述吡啶基、嘧啶基、吡嗪基和三嗪基分别选自:中取代的任意一种。
优选的,所述铱配合物具有如下结构之一:
本发明还提供所述铱配合物的制备方法:将含有两个主配体的铱二聚桥连配合物和2-(5-苯基-1,3,4-恶二唑-2-)苯酚辅助配体及碳酸钠混合;所述主配体为2-(4,6-二三氟甲基吡啶-3-)基吡啶、2-(4,6-二三氟甲基吡啶-4-)基吡啶、2-(4,6-二三氟甲基吡啶-3-)基嘧啶、2-(4,6-二三氟甲基吡啶-4-)基嘧啶、2-(4,6-二三氟甲基吡啶-3-)基吡嗪、2-(4,6-二三氟甲基吡啶-4-)基吡嗪和2-(4,6-二三氟甲基吡啶-3-)基三嗪、2-(4,6-二三氟甲基吡啶-4-)基三嗪衍生物中的任意一种;加入2-乙氧基乙醇溶液,在120-140℃下进行加热反应,反应时间12-48h,冷却至室温,减压蒸馏除去溶剂,再用二氯甲烷萃取,浓缩,经柱层析分离,得到配合物的粗品,经升华得到纯的铱配合物。
优选的,所述铱二聚桥连配合物、辅助配体和碳酸钠的摩尔比为1∶2∶5。
本发明还提供一种应用该铱配合物的电致发光器件,其包括基片、阳极、空穴传输层、有机发光层、电子传输层和阴极,所述基片为玻璃,阳极为铟锡氧,空穴层采用TAPC材料,电子传输层采用TmPyPB材料制备,所述有机发光层包括主体材料和发光材料,所述主体材料是1,3-二(9H-咔唑-9-基)苯mCP,所述发光材料包括所述的铱配合物。
本发明的有益效果:本发明提供的铱配合物具有发光效率高、电子迁移率高和化学性质稳定、易升华提纯的特点。所述铱配合物的制备方法简单,产率较高。由于氮杂环的引入,配合物的电子传输性能能够有效调控,为有机电致发光显示器以及照明光源的设计生产提供了便利。所述电致发光器件的性能优良。
【附图说明】
图1为本发明提供的铱配合物GIr8-001用于有机电致发光器件的电致发光光谱;
图2为本发明提供的铱配合物GIr8-001用于有机电致发光器件的光电性能;
图3为本发明提供的铱配合物GIr8-001用于有机电致发光器件的光电性能。
【具体实施方式】
下面结合附图和实施例进一步详细描述本发明。在本发明中所使用的术语,除非另有说明,一般具有本领域普通技术人员通常理的含义。
本发明的铱配合物在合成过程中都用到了三氯化铱、4,6-二三氟甲基吡啶-3-硼酸、4,6-二三氟甲基吡啶-4-硼酸、2-溴吡啶衍生物、2-溴嘧啶衍生物、2-溴吡嗪衍生物和2-溴三嗪衍生物等,合成方法类似。将含有两个主配体的铱二聚桥连配合物和2-(5-苯基-1,3,4-恶二唑-2-)苯酚辅助配体及碳酸钠混合;所述主配体为2-(4,6-二三氟甲基吡啶-3-)基吡啶、2-(4,6-二三氟甲基吡啶-4-)基吡啶、2-(4,6-二三氟甲基吡啶-3-)基嘧啶、2-(4,6-二三氟甲基吡啶-4-)基嘧啶、2-(4,6-二三氟甲基吡啶-3-)基吡嗪、2-(4,6-二三氟甲基吡啶-4-)基吡嗪和2-(4,6-二三氟甲基吡啶-3-)基三嗪、2-(4,6-二三氟甲基吡啶-4-)基三嗪衍生物中的任意一种;加入2-乙氧基乙醇溶液,在120-140摄氏度下进行加热反应,反应时间12-48h,冷却至室温,减压蒸馏除去溶剂,再用二氯甲烷萃取,浓缩,经柱层析分离,得到配合物的粗品,经升华提纯得到铱配合物。其中,所述铱二聚桥连配合物含有2-(4,6-二三氟甲基吡啶-3-)基吡啶、2-(4,6-二三氟甲基吡啶-4-)基吡啶、2-(4,6-二三氟甲基吡啶-3-)基嘧啶、2-(4,6-二三氟甲基吡啶-4-)基嘧啶、2-(4,6-二三氟甲基吡啶-3-)基吡嗪、2-(4,6-二三氟甲基吡啶-4-)基吡嗪和2-(4,6-二三氟甲基吡啶-3-)基三嗪、2-(4,6-二三氟甲基吡啶-4-)基三嗪衍生物中的任意一种,所述铱二聚桥连配合物、辅助配体和碳酸钠的摩尔比为1∶2∶5。
所述铱配合物具有如下结构之一:
下面以其中一实施例,配合物GIr8-001为例具体说明本发明内容,通过下述实施例将有助于进一步理解本发明,但不限制本发明的内容。
配合物GIr8-001的合成方法
2-溴吡啶(26.39mmol)、4,6-二三氟甲基吡啶-3-硼酸(31.66mmol)、四三苯基磷钯(0.79mmol)和碳酸钠(60.00mmol)溶解在100mL四氢呋喃中,65℃反应24小时,冷却,加入水和二氯甲烷,有机层浓缩柱层析得到主配体(产率为52.24%)。将主配体(13.08mmol)和三氯化铱(6.23mmol)溶于15mL 2-乙氧基乙醇中,混合物130℃反应12h,然后加入2-(5-苯基-1,3,4-恶二唑-2-)苯酚(12.46mmol)和碳酸钠(31.15mmol),继续130℃反应24h。体系冷却,加入水和二氯甲烷,有机层浓缩柱层析得黄色固体GIr8-001(产率为44%)。
核磁及质谱表征:1H NMR(500MHz,CDCl3)δ9.09(d,J=5.6Hz,2H),8.29(d,J=8.4Hz,2H),7.66(t,J=8.0Hz,2H),7.16(t,J=7.4Hz,2H),7.32(t,J=6.6Hz,1H),7.18-7.14(m,3H),6.83(t,J=6.5Hz,2H),6.59(d,J=8.6Hz,2H),6.49(t,J=7.4Hz,1H),6.42(s,1H),6.28(s,1H).ESI-MS:m/z1012.10[M]+,found:1011.79[M]+.
本发明以2-(4,6-二三氟甲基吡啶-3-)基吡啶、2-(4,6-二三氟甲基吡啶-4-)基吡啶、2-(4,6-二三氟甲基吡啶-3-)基嘧啶、2-(4,6-二三氟甲基吡啶-4-)基嘧啶、2-(4,6-二三氟甲基吡啶-3-)基吡嗪、2-(4,6-二三氟甲基吡啶-4-)基吡嗪和2-(4,6-二三氟甲基吡啶-3-)基三嗪、2-(4,6-二三氟甲基吡啶-4-)基三嗪衍生物中的任意一种作为主配体,以2-(5-苯基-1,3,4-恶二唑-2-)苯酚为辅助配体,设计合成了一系列绿光铱配合物。通过设计配体或配合物结构,并通过在配体上简单的化学取代基的修饰,达到调控配合物发光和电子迁移率的目的。
所述氮杂环均是具较强电子传输性的基团,有力于平衡载流子的注入与传输。
所述铱配合物具有较高的发光效率和电子迁移率,经优化验证后,其制备方法简单,且产率较高。
有机电致发光器件的制备
下面以GIr8-001作为发光材料制备有机电致发光器件为例,说明本发明有机电致发光器件的制备。OLEDs器件的结构包括:基片、阳极、空穴传输层、有机发光层和电子传输层/阴极。
在本发明的器件制作中基片为玻璃,阳极材料为铟锡氧(ITO);空穴传输层使用4,4′-环己基二[N,N-二(4-甲基苯基)苯胺(TAPC),电子传输层材料使用3,3′-(5′-(3-(吡啶-3-基)苯基)-[1,1′:3′,1″-三苯基]-3,3″-二基)二吡啶(TmPyPB),厚度为60nm,蒸镀速率为0.05nm/s;阴极采用LiF/Al,LiF厚度为1nm,蒸镀速率为0.01nm/s,Al厚度为100nm,蒸镀速率为0.2nm/s。有机发光层采用掺杂结构,主体材料是用1,3-二(9H-咔唑-9-基)苯(mCP),所选用的发光材料是GIr8-001。发光层厚度为40nm,蒸镀速率为0.05nm/s,GIr8-001质量分数8%。
本发明中用的几种材料结构如下:
本发明选择一种绿光配合物制备有机电致发光器件。请一并参阅图1、图2及图3,图1为本发明提供的铱配合物用于有机电致发光器件的电致发光光谱,图2和图3为本发明提供的铱配合物用于有机电致发光器件的光电性能。如图2和图3所示,所述有机电致发光器件的最大功率效率和电流效率分别为32.25lm/W和66.94cd/A,最大亮度33343cd/m2。通过研究光物理性质,表明这类含有氮杂环的磷光铱配合物具有较高的器件效率,在显示和照明等领域具有实际应用价值。
本发明提供的该类磷光材料可作为发光中心应用于磷光OLEDs的发射层,通过设计配体或配合物结构,并通过对所述配体的化学取代基进行修饰,本发明达到了调控配合物发光颜色和效率的目的。
以上所述的仅是本发明的实施方式,在此应当指出,对于本领域的普通技术人员来说,在不脱离本发明创造构思的前提下,还可以做出改进,但这些均属于本发明的保护范围。
Claims (7)
1.一种铱配合物,其特征在于,其含有两个主配体和一个2-(5-苯基-1,3,4-恶二唑-2-)苯酚辅助配体,所述主配体为2-(4,6-二三氟甲基吡啶-3-)基吡啶、2-(4,6-二三氟甲基吡啶-4-)基吡啶、2-(4,6-二三氟甲基吡啶-3-)基嘧啶、2-(4,6-二三氟甲基吡啶-4-)基嘧啶、2-(4,6-二三氟甲基吡啶-3-)基吡嗪、2-(4,6-二三氟甲基吡啶-4-)基吡嗪和2-(4,6-二三氟甲基吡啶-3-)基三嗪、2-(4,6-二三氟甲基吡啶-4-)基三嗪衍生物中的任意一种,所述主配体中,和铱以C原子配位的吡啶衍生物为:所述吡啶衍生物和不同主配体中的吡啶基、嘧啶基、吡嗪基和三嗪基的连接位置不同;所述吡啶基、嘧啶基、吡嗪基和三嗪基的任意位被卤素或烷基取代,所述吡啶基上取代基的数量为0-4,所述嘧啶基和吡嗪基上取代基的数量为0-3,所述三嗪基上取代基的数量为0-2。
2.根据权利要求1所述的铱配合物,其特征在于,所述卤素为F,所述烷基为三氟甲基、甲基中的任意一种。
3.根据权利要求2所述的铱配合物,其特征在于,所述主配中的4,6-二三氟甲基吡啶在不同主配体中和吡啶基、嘧啶基、吡嗪基和三嗪基连接的位置不同,取自3位和4位;所述吡啶基、嘧啶基、吡嗪基和三嗪基分别选自:中取代的任意一种。
4.根据权利要求3所述的铱配合物,其特征在于,所述铱配合物具有如下结构之一:
5.一种铱配合物的制备方法,其特征在于,将含有两个主配体的铱二聚桥连配合物和2-(5-苯基-1,3,4-恶二唑-2-)苯酚辅助配体及碳酸钠混合;所述主配体为2-(4,6-二三氟甲基吡啶-3-)基吡啶、2-(4,6-二三氟甲基吡啶-4-)基吡啶、2-(4,6-二三氟甲基吡啶-3-)基嘧啶、2-(4,6-二三氟甲基吡啶-4-)基嘧啶、2-(4,6-二三氟甲基吡啶-3-)基吡嗪、2-(4,6-二三氟甲基吡啶-4-)基吡嗪和2-(4,6-二三氟甲基吡啶-3-)基三嗪、2-(4,6-二三氟甲基吡啶-4-)基三嗪衍生物中的任意一种;加入2-乙氧基乙醇溶液,在120-140℃下进行加热反应,反应时间12-48h,冷却至室温,减压蒸馏除去溶剂,再用二氯甲烷萃取,浓缩,经柱层析分离,得到配合物的粗品,经升华得到纯的铱配合物。
6.根据权利要求5所述的铱配合物的制备方法,其特征在于,所述铱二聚桥连配合物和2-(5-苯基-1,3,4-恶二唑-2-)苯酚、碳酸钠的摩尔比为1∶2∶5。
7.一种应用如权利要求1-4任一项所述铱配合物的电致发光器件,其包括基片、阳极、空穴传输层、有机发光层、电子传输层和阴极,所述基片为玻璃,阳极为铟锡氧,空穴层采用TAPC材料,电子传输层采用TmPyPB材料,所述有机发光层包括主体材料和发光材料,所述主体材料是1,3-二(9H-咔唑-9-基)苯mCP,所述发光材料包括所述的铱配合物。
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