Synthesis and Properties of Near Infrared-emitting Iridium（Ⅲ） Complexes with Auxiliary Ligand Functionalized

CHEN Jun; XU Ying; XU Chao; FAN Wei-xue; YU Jun-ting; TAN Hua

doi:10.37188/CJL.20220114

您当前的位置：

首页 >

文章列表页 >

Synthesis and Properties of Near Infrared-emitting Iridium（Ⅲ） Complexes with Auxiliary Ligand Functionalized

Synthesis and Properties of Materials | 更新时间：2022-10-19

- Synthesis and Properties of Near Infrared-emitting Iridium（Ⅲ） Complexes with Auxiliary Ligand Functionalized
  增强出版
- Chinese Journal of Luminescence Vol. 43, Issue 8, Pages: 1217-1226(2022)
- 作者机构：
  
  1.常州大学材料科学与工程学院江苏省光电热能量转化材料与应用工程实验室，江苏常州　213164
  2.湘潭大学化学学院，湖南湘潭　411105
- 作者简介：
- 基金信息：
  
  The Open Project of Jiangsu Photoelectric Thermal Energy Conversion Materials and Application Engineering Laboratory(GDRGCS2020001);Postgraduate Research ＆ Practice Innovation Program of Jiangsu Province(SJCX21_1247)
- DOI：10.37188/CJL.20220114
  CLC： O614
- Published：05 August 2022，
  
  Received：29 March 2022，
  
  Revised：12 April 2022，
- 稿件说明：
移动端阅览
陈俊,徐颖,徐超等.辅助配体功能化铱（Ⅲ）配合物近红外电致发光材料的合成及其性能[J].发光学报,2022,43(08):1217-1226.

CHEN Jun,XU Ying,XU Chao,et al.Synthesis and Properties of Near Infrared-emitting Iridium（Ⅲ） Complexes with Auxiliary Ligand Functionalized[J].Chinese Journal of Luminescence,2022,43(08):1217-1226.
陈俊,徐颖,徐超等.辅助配体功能化铱（Ⅲ）配合物近红外电致发光材料的合成及其性能[J].发光学报,2022,43(08):1217-1226. DOI： 10.37188/CJL.20220114.

CHEN Jun,XU Ying,XU Chao,et al.Synthesis and Properties of Near Infrared-emitting Iridium（Ⅲ） Complexes with Auxiliary Ligand Functionalized[J].Chinese Journal of Luminescence,2022,43(08):1217-1226. DOI： 10.37188/CJL.20220114.

摘要

将烷基芴（Fluorene，FL）基团通过柔性烷基链连接到吡啶甲酸（Picolinic acid，pic）上，合成了辅助配体功能化的供体‐受体（D‐A）型铱配合物近红外电致发光材料（CH

OTPA‐BTz‐Iq）

Ir（pic‐FL）（TPA：Triphenylamine为三苯胺，BTz：Benzotriazole为苯并三唑，Iq：Isoquinoline为异喹啉）。通过对其紫外‐可见吸收光谱和光致发光光谱研究发现，由于主配体中强D‐A作用的CH

OTPA‐BTz结构，配合物具有强分子内电荷转移跃迁（Charge transfer transition，ICT）吸收峰和720 nm左右的光致发光峰。与此同时，（CH

OTPA‐BTz‐Iq）

Ir（pic‐FL）分子中柔性烷基链和高荧光量子效率芴基团的引入，可以提高材料光致发光效率，改善材料的溶解性能和器件成膜性能，提高电致发光效率。以配合物为发光掺杂剂制备的有机电致发光器件其最大发射峰位于722 nm左右的近红外区域，最大外量子效率（EQE

max

）为0.92%，是其母体配合物（CH

OTPA‐BTz‐Iq）

‐Irpic器件效率的2.24倍（EQE

max

为0.41%@723 nm）。

Abstract

In this paper， a novel auxiliary ligand functionalized donor-acceptor（D-A） type near infrared-emitting iridium（Ⅲ） complex （CH

OTPA-BTz-Iq）

Ir（pic-FL） was synthesized by connecting alkylfluorene（FL） to picolinic acid（pic）. Through the study of UV-Vis absorption and photoluminescence spectrum， the complex has a strong intramolecular charge transfer transition （ICT） absorption peak and a photoluminescence peak about 720 nm due to the strong D-A effect of the CH

OTPA-BTz-Iq ligand. Furthermore， the photoluminescence and electroluminescent properties of （CH

OTPA-BTz-Iq）

Ir（pic-FL） were improved by introducing alkyl chains and FL group with high fluorescence quantum efficiency， good solubility and film forming performance. In （CH

OTPA-BTz-Iq）

Ir‐（pic-FL）-based OLEDs， a maximum external quantum efficiency （EQE

max

） of 0.92% at 722 nm was obtained， which is much superior than that of the （CH

OTPA-BTz-Iq）

Irpic-based OLEDs （0.41% at 723 nm）.

关键词

铱（Ⅲ）配合物芴供体-受体近红外电致发光

Keywords

iridium（Ⅲ） complexfluorenedonor-acceptornear infraredelectroluminescence

references

LY K T， CHEN-CHENG R W， LIN H W， et al. Near-infrared organic light-emitting diodes with very high external quantum efficiency and radiance ［J］. Nat. Photonics， 2017， 11（1）： 63-68. doi: 10.1038/nphoton.2016.230http://dx.doi.org/10.1038/nphoton.2016.230

WANG S F， YUAN Y， WEI Y C， et al. Highly efficient near-infrared electroluminescence up to 800 nm using platinum（Ⅱ） phosphors ［J］. Adv. Funct. Mater.， 2020， 30（30）： 2002173-1-9. doi: 10.1002/adfm.202002173http://dx.doi.org/10.1002/adfm.202002173

常鹏，韩春苗，许辉. 近红外有机小分子电致发光材料研究进展［J］. 液晶与显示， 2021， 36（1）： 62-77. doi: 10.37188/CJLCD.2020-0207http://dx.doi.org/10.37188/CJLCD.2020-0207

CHANG P， HAN C M， XU H. Research progress of near infrared organic small-molecule electroluminescent materials ［J］. Chin. J. Liq. Cryst. Disp.， 2021， 36（1）： 62-77. （in Chinese）. doi: 10.37188/CJLCD.2020-0207http://dx.doi.org/10.37188/CJLCD.2020-0207

张松涛，王樱蕙，张洪杰. 稀土发光材料在近红外二区成像中的应用［J］. 发光学报， 2020， 41（12）： 1460-1478. doi: 10.37188/CJL.20200340http://dx.doi.org/10.37188/CJL.20200340

ZHANG S T， WANG Y H， ZHANG H J. Lanthanide-doped fluorescence probes for NIR-Ⅱ fluorescence imaging ［J］. Chin. J. Lumin.， 2020， 41（12）： 1460-1478. （in Chinese）. doi: 10.37188/CJL.20200340http://dx.doi.org/10.37188/CJL.20200340

BALIJAPALLI U， NAGATA R， YAMADA N， et al. Highly efficient near-infrared electrofluorescence from a thermally activated delayed fluorescence molecule ［J］. Angew. Chem.， Int. Ed.， 2021， 60（15）： 8477-8482. doi: 10.1002/anie.202016089http://dx.doi.org/10.1002/anie.202016089

JACKSON C T， JEONG S， DORLHIAC G F， et al. Advances in engineering near-infrared luminescent materials ［J］. iScience， 2021， 24（3）： 102156-1-21. doi: 10.1016/j.isci.2021.102156http://dx.doi.org/10.1016/j.isci.2021.102156

ZHANG Y X， QIAO J. Near-infrared emitting iridium complexes： molecular design， photophysical properties， and related applications ［J］. iScience， 2021， 24（8）： 102858. doi: 10.1016/j.isci.2021.102858http://dx.doi.org/10.1016/j.isci.2021.102858

周港杰，胡艺萱，谭林玲，等. 碲掺杂钙-铝-锗酸盐玻璃宽带近红外发光及其调控机理［J］. 发光学报， 2022， 43（1）： 51-57. doi: 10.37188/CJL.20210337http://dx.doi.org/10.37188/CJL.20210337

ZHOU G J， HU Y X， TAN L L， et al. Broadband near-infrared luminescence and regulation mechanism of tellurium-doped calcium-aluminum-germanate glass ［J］. Chin. J. Lumin.， 2022， 43（1）： 51-57. （in Chinese）. doi: 10.37188/CJL.20210337http://dx.doi.org/10.37188/CJL.20210337

徐冀健，曲丹，安丽，等. 红光/近红外发射碳点制备、光学调控与应用［J］. 发光学报， 2021， 42（12）： 1837-1851. doi: 10.37188/CJL.20210302http://dx.doi.org/10.37188/CJL.20210302

XU J J， QU D， AN L， et al. Preparation， optical control and application of red/near infrared emitting carbon dots ［J］. Chin. J. Lumin.， 2021， 42（12）： 1837-1851. （in Chinese）. doi: 10.37188/CJL.20210302http://dx.doi.org/10.37188/CJL.20210302

WILLIAMS E L， LI J， JABBOUR G E， et al. Organic light-emitting diodes having exclusive near-infrared electrophosphorescence ［J］. Appl. Phys. Lett.， 2006， 89（8）： 083506-1-3. doi: 10.1063/1.2335275http://dx.doi.org/10.1063/1.2335275

QIAO J， DUAN L， TANG L T， et al. High-efficiency orange to near-infrared emissions from bis-cyclometalated iridium complexes with phenyl-benzoquinoline isomers as ligands ［J］. J. Mater. Chem.， 2009， 19（36）： 6573-6580. doi: 10.1039/b906675fhttp://dx.doi.org/10.1039/b906675f

TAO R， QIAO J， ZHANG G L， et al. Efficient near-infrared-emitting cationic iridium complexes as dopants for OLEDs with small efficiency roll-off ［J］. J. Phys. Chem. C， 2012， 116（21）： 11658-11664. doi: 10.1021/jp301740chttp://dx.doi.org/10.1021/jp301740c

TAO R， QIAO J， ZHANG G L， et al. High-efficiency near-infrared organic light-emitting devices based on an iridium complex with negligible efficiency roll-off ［J］. J. Mater. Chem. C， 2013， 1（39）： 6446-6454. doi: 10.1039/c3tc30866ahttp://dx.doi.org/10.1039/c3tc30866a

CAO X S， MIAO J S， ZHU M R， et al. Near-infrared polymer light-emitting diodes with high efficiency and low efficiency roll-off by using solution-processed iridium（Ⅲ） phosphors ［J］. Chem. Mater.， 2015， 27（1）： 96-104. doi: 10.1021/cm503361jhttp://dx.doi.org/10.1021/cm503361j

XIN L J， Xue J， Lei G T， et al. Efficient near-infrared-emitting cationic iridium complexes based on highly conjugated cyclometalated benzo［g］phthalazine derivatives ［J］. RSC Adv.， 2015， 5（53）： 42354-42361. doi: 10.1039/c5ra04511hhttp://dx.doi.org/10.1039/c5ra04511h

KESARKAR S， MRÓZ W， PENCONI M， et al. Near-IR emitting iridium（Ⅲ） complexes with heteroaromatic β-diketonate ancillary ligands for efficient solution-processed OLEDs： structure-property correlations ［J］. Angew. Chem.， Int. Ed.， 2016， 55（8）： 2714-2718. doi: 10.1002/anie.201509798http://dx.doi.org/10.1002/anie.201509798

XUE J， XIN L J， HOU J Y， et al. Homoleptic facial Ir（Ⅲ） complexes via facile synthesis for high-efficiency and low-roll-off near-infrared organic light-emitting diodes over 750 nm ［J］. Chem. Mater.， 2017， 29（11）： 4775-4782. doi: 10.1021/acs.chemmater.7b00518http://dx.doi.org/10.1021/acs.chemmater.7b00518

CHEN Z， WANG L Q， HO C L， et al. Smart design on the cyclometalated ligands of iridium（Ⅲ） complexes for facile tuning of phosphorescence color spanning from deep-blue to near-infrared ［J］. Adv. Opt. Mater.， 2018， 6（23）： 1800824. doi: 10.1002/adom.201800824http://dx.doi.org/10.1002/adom.201800824

CHEN Z， ZHANG H Y， WEN D W， et al. A simple and efficient approach toward deep-red to near-infrared-emitting iridium（Ⅲ） complexes for organic light-emitting diodes with external quantum efficiencies of over 10% ［J］. Chem. Sci.， 2020， 11（9）： 2342-2349. doi: 10.1039/c9sc05492hhttp://dx.doi.org/10.1039/c9sc05492h

YOU C F， LIU D H， YU J T， et al. Boosting efficiency of near-infrared emitting iridium（Ⅲ） phosphors by administrating their π‐π conjugation effect of core-shell structure in solution-processed OLEDs ［J］. Adv. Opt. Mater.， 2020， 8（18）： 2000154-1-10. doi: 10.1002/adom.202000154http://dx.doi.org/10.1002/adom.202000154

YU J T， LI M Q， XU C， et al. Near-infrared cyclometalated iridium（Ⅲ） complexes with bipolar features for efficient OLEDs via solution-processing ［J］. Dalton Trans.， 2020， 49（25）： 8785-8790. doi: 10.1039/d0dt01415jhttp://dx.doi.org/10.1039/d0dt01415j

ZHANG Y X， LI Q， CAI M H， et al. An 850 nm pure near-infrared emitting iridium complex for solution-processed organic light-emitting diodes ［J］. J. Mater. Chem. C， 2020， 8（25）： 8484-8492. doi: 10.1039/d0tc01614dhttp://dx.doi.org/10.1039/d0tc01614d

LEE S Y， YASUDA T， YANG Y S， et al. Luminous butterflies： efficient exciton harvesting by benzophenone derivatives for full-color delayed fluorescence OLEDs ［J］. Angew. Chem.， Int. Ed.， 2014， 53（25）： 6402-6406. doi: 10.1002/anie.201402992http://dx.doi.org/10.1002/anie.201402992

YAN Y， SUN N W， LI F F， et al. Multiple stimuli-responsive fluorescence behavior of novel polyamic acid bearing oligoaniline， triphenylamine， and fluorene groups ［J］. ACS Appl. Mater. Interfaces， 2017， 9（7）： 6497-6503. doi: 10.1021/acsami.6b16402http://dx.doi.org/10.1021/acsami.6b16402

YU J T， TAN H， MENG F Y， et al. Benzotriazole-containing donor-acceptor-acceptor type cyclometalated iridium（Ⅲ） complex for solution-processed near-infrared polymer light emitting diodes ［J］. Dyes Pigments， 2016， 131： 231-238. doi: 10.1016/j.dyepig.2016.04.021http://dx.doi.org/10.1016/j.dyepig.2016.04.021

WANG Y F， TAN H， LIU Y， et al. Synthesis， opto-physics， and electroluminescence of cyclometalated iridium （Ⅲ） complex with alkyltrifluorene picolinic acid ［J］. Tetrahedron， 2010， 66（7）： 1483-1488. doi: 10.1016/j.tet.2009.12.001http://dx.doi.org/10.1016/j.tet.2009.12.001

Views

300

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Research Progress of Neutral Blue Iridium Complexes in OLEDs

Efficient Red Iridium（Ⅲ） Complexes with Four-membered Ring Ir-S-C-S Framework and OLED Performance

Performance of Narrow-linewidth Red Emitted Electroluminescent Devices Based on Quasi-two-dimensional Perovskite

Enhanced Electroluminescence Properties of Tin-based Perovskites by Vitamin C Additives

Related Author

Jun CHEN

Ying XU

Chao XU

Wei-xue FAN

Jun-ting YU

Hua TAN

WU Shaohua

LU Guangzhao

Related Institution

Jiangsu Engineering Laboratory of Light-Electricity-Heat Energy-Converting Materials and Applications，School of Materials Science and Engineering， Changzhou University

Institute of Information Technology， Shenzhen Institute of Information Technology

College of Chemistry and Materials Science， Hebei Normal University

College of Chemistry and Chemical Engineering， Shangqiu Normal University

State Key Laboratory of Rare Earth Resource Utilization， Changchun Institute of Applied Chemistry， Chinese Academy of Sciences

Address：No.3888 Dong Nanhu Road, Changchun, Jilin, China Postal code：130033
Tel：0431-86176862 Email：fgxbt@126.com
Technical support is provided by Beijing Founder electronics co., LTD 吉ICP备11002662号-17 京公网安备11010802024621
It is recommended to read the content of this site in Chrome&IE9+. Please switch to extreme mode in browser 360.
Cookies We use cookies to help provide and enhance our service and tailor content. By continuing, you agree to the use of cookies.

⁰