Synthesis and Characterization of Aggregation-induced Red Emitter Based on Dibenzophenazine Core

XING Yifan; SHI Mingkai; LI Zhijun; LI Da; DONG Linlin; LUO Yang; ZHAO Shijie; XIE Tianyou; WANG Hua; GUO Kunpeng; MIAO Yanqin

doi:10.37188/CJL.20230096

您当前的位置：

首页 >

文章列表页 >

Synthesis and Characterization of Aggregation-induced Red Emitter Based on Dibenzophenazine Core

Synthesis and Properties of Materials | 更新时间：2023-09-28

- Synthesis and Characterization of Aggregation-induced Red Emitter Based on Dibenzophenazine Core
  增强出版
- Chinese Journal of Luminescence Vol. 44, Issue 9, Pages: 1588-1596(2023)
- 作者机构：
  
  太原理工大学新材料界面科学与工程教育部重点实验室，山西太原　030024
- 作者简介：
- 基金信息：
  
  国家自然科学基金(62074109;6207031407);Science and Technology Innovation Talent Team Project of Shanxi Province(202204051001013)
- DOI：10.37188/CJL.20230096
  CLC： O482.31
- Published：05 September 2023，
  
  Received：17 April 2023，
  
  Revised：05 May 2023，
扫描看全文
邢艺凡,石明恺,李芷君等.以二苯并吩嗪为核心的聚集诱导发红光材料制备及表征[J].发光学报,2023,44(09):1588-1596.

XING Yifan,SHI Mingkai,LI Zhijun,et al.Synthesis and Characterization of Aggregation-induced Red Emitter Based on Dibenzophenazine Core[J].Chinese Journal of Luminescence,2023,44(09):1588-1596.
邢艺凡,石明恺,李芷君等.以二苯并吩嗪为核心的聚集诱导发红光材料制备及表征[J].发光学报,2023,44(09):1588-1596. DOI： 10.37188/CJL.20230096.

XING Yifan,SHI Mingkai,LI Zhijun,et al.Synthesis and Characterization of Aggregation-induced Red Emitter Based on Dibenzophenazine Core[J].Chinese Journal of Luminescence,2023,44(09):1588-1596. DOI： 10.37188/CJL.20230096.

摘要

有机红光材料在全色显示、生物成像及荧光探针等方面有着重要的应用前景。本文以电子受体二苯并吩嗪为核，在其3，6位引入给电子基二苯胺衍生物，在其11，12位引入拉电子基吡啶，设计并合成了一种具有给⁃受体结构的化合物

DBPAP

。通过元素分析、核磁共振波谱和质谱对化合物的化学结构进行了表征与确认。荧光发射光谱表征发现，

DBPAP

在四氢呋喃和水的混合溶剂中随不良溶剂水含量增加呈现出典型的聚集诱导发光现象。基于其在固态下的有效红光发射，将

DBPAP

掺杂到PMMA中制备了红光LED器件。在3.8 V工作电压下，器件的最大发射波长为644 nm，CIE坐标为（0.58，0.35），最大亮度为1 616 cd·m

-2

。该工作为发展新型固态有机红光材料提供了重要思路。

Abstract

Organic red emitters have attracted significant research attention owing to their promising applications in panchromatic display， biological imaging， and fluorescent probes. Herein， a fluorescent compound

DBPAP

was developed by introducing electron-donating group diphenylamine derivative at the positions of 3 and 6， and electron-withdrawing group pyridine at the positions of 11 and 12 of dibenzophenazine core. Its chemical structure was characterized and confirmed by elemental analysis， nuclear magnetic resonance spectroscopy and mass spectroscopy. Spectroscopic results showed that the addition of the poor solvent water to the tetrahydrofuran solution of

DBPAP

caused obvious aggregation-induced emission （AIE） phenomenon. Based on its efficient red emission in solid state， LED devices based on

DBPAP

doped PMMA were fabricated. The devices exhibited a red emission at 644 nm with Commission Internationale de L’Éclairage coordinates of （0.58， 0.35）， and a maximum brightness of 1 616 cd·m

-2

at a 3.8 V work voltage. This work provides a promising strategy for developing solid-state red emissive organics.

关键词

有机红光材料二苯并吩嗪给-受体聚集诱导发光红光LED

Keywords

organic red emittersdibenzophenazinedonor-acceptoraggregation-induced emissionred LED

references

赵伟明，张步新，朱文清，等. 红色有机发光二极管［J］. 光学学报， 2001， 21（1）： 79-82. doi: 10.3321/j.issn:0253-2239.2001.01.019http://dx.doi.org/10.3321/j.issn:0253-2239.2001.01.019

ZHAO W M， ZHANG B X， ZHU W Q， et al. Red organic electroluminescence devices ［J］. Acta Opt. Sinica， 2001， 21（1）： 79-82. （in Chinese）. doi: 10.3321/j.issn:0253-2239.2001.01.019http://dx.doi.org/10.3321/j.issn:0253-2239.2001.01.019

马东阁. OLED显示与照明——从基础研究到未来的应用［J］. 液晶与显示， 2016， 31（3）： 229-241. doi: 10.3788/yjyxs20163103.0229http://dx.doi.org/10.3788/yjyxs20163103.0229

MA D G. OLED display and lighting-from basic research to future applications ［J］. Chin. J. Liq. Cryst. Disp.， 2016， 31（3）： 229-241. （in Chinese）. doi: 10.3788/yjyxs20163103.0229http://dx.doi.org/10.3788/yjyxs20163103.0229

尹茂军，潘腾，刘士浩，等. CdSe/ZnS量子点下转换膜的红、绿、蓝顶发射有机发光器件［J］. 中国光学， 2019， 12（6）： 1431-1441. doi: 10.3788/co.20191206.1431http://dx.doi.org/10.3788/co.20191206.1431

YIN M J， PAN T， LIU S H， et al. Top-emitting red， green and blue organic light-emitting devices with CdSe/ZnS quantum dots down-conversion films ［J］. Chin. Opt.， 2019， 12（6）： 1431-1441. （in Chinese）. doi: 10.3788/co.20191206.1431http://dx.doi.org/10.3788/co.20191206.1431

陈孔岚，张学亮，宋恩海，等. CaTiF6·2H2O∶Mn4+窄带红色荧光粉的发光性能及其高显指暖白光LED应用［J］. 发光学报， 2023， 44（2）： 259-270.

CHEN K L， ZHANG X L， SONG E H， et al. Luminescence properties of Narrow-band red phosphor CaTiF6·2H2O∶Mn4+ for warm white light-emitting diodes with high color rendering index ［J］. Chin. J. Lumin.， 2023， 44（2）： 259-270. （in Chinese）

李新贝，张方辉，张麦丽. 掺杂型红色有机电致发光显示器件［J］. 发光学报， 2006， 27（5）： 689-694. doi: 10.3321/j.issn:1000-7032.2006.05.011http://dx.doi.org/10.3321/j.issn:1000-7032.2006.05.011

LI X B， ZHANG F H， ZHANG M L. Red doped organic light-emitting diodes ［J］. Chin. J. Lumin.， 2006， 27（5）： 689-694. （in Chinese）. doi: 10.3321/j.issn:1000-7032.2006.05.011http://dx.doi.org/10.3321/j.issn:1000-7032.2006.05.011

冯奇斌，尹慧娟，李亚妮，等. 用于机载液晶显示的四基色发光二极管背光源［J］. 光学精密工程， 2015， 23（9）： 2459-2465. doi: 10.3788/ope.20152309.2459http://dx.doi.org/10.3788/ope.20152309.2459

FENG Q B， YIN H J， LI Y N， et al. 4-primary-color-based LED backlight for aircraft cockpit LCD ［J］. Opt. Precision Eng.， 2015， 23（9）： 2459-2465. （in Chinese）. doi: 10.3788/ope.20152309.2459http://dx.doi.org/10.3788/ope.20152309.2459

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

YAN Q， YAN J K， ZHOU J H， et al. Regulation of fluorescent color and efficiency by molecular symmetry engineering of triphenylamine-based red emitters and their applications ［J］. Opt. Mater.， 2023， 136： 113435. doi: 10.1016/j.optmat.2023.113435http://dx.doi.org/10.1016/j.optmat.2023.113435

ENGLMAN R， JORTNER J. The energy gap law for non-radiative decay in large molecules ［J］. J. Lumin.， 1970， 1-2： 134-142. doi: 10.1016/0022-2313(70)90029-3http://dx.doi.org/10.1016/0022-2313(70)90029-3

MINOTTO A， MURTO P， GENENE Z， et al. Efficient near-infrared electroluminescence at 840 nm with “Metal-Free” small-molecule： polymer blends ［J］. Adv. Mater.， 2018， 30（34）： 1706584-1-9. doi: 10.1002/adma.201706584http://dx.doi.org/10.1002/adma.201706584

ZHANG D， YANG T T， XU H X， et al. Triphenylamine/benzothiadiazole-based compounds for non-doped orange and red fluorescent OLEDs with high efficiencies and low efficiency roll-off ［J］. J. Mater. Chem. C， 2021， 9（14）： 4921-4926. doi: 10.1039/d1tc00249jhttp://dx.doi.org/10.1039/d1tc00249j

MA X F， SUN R， CHENG J H， et al. Fluorescence aggregation-caused quenching versus aggregation-induced emission： a visual teaching technology for undergraduate chemistry students ［J］. J. Chem. Educ.， 2016， 93（2）： 345-350. doi: 10.1021/acs.jchemed.5b00483http://dx.doi.org/10.1021/acs.jchemed.5b00483

贾钧森，王飞，赵波，等. D-π-A-π-D型小分子红光材料的制备及其性能［J］. 发光学报， 2020， 41（1）： 9-15. doi: 10.3788/fgxb20204101.0009http://dx.doi.org/10.3788/fgxb20204101.0009

JIA J S， WANG F， ZHAO B， et al. Design， synthesis and properties of D-π-A-π-D type organic red light luminogens ［J］. Chin. J. Lumin.， 2020， 41（1）： 9-15. （in Chinese）. doi: 10.3788/fgxb20204101.0009http://dx.doi.org/10.3788/fgxb20204101.0009

GAO Z X， ZHANG F， GAO L， et al. An A-D-A type of thiophene derivative with morphology-determining luminescent performance： synthesis and application in a light emitting device ［J］. J. Lumin.， 2020， 219： 116919. doi: 10.1016/j.jlumin.2019.116919http://dx.doi.org/10.1016/j.jlumin.2019.116919

秦安军，胡蓉. 聚集诱导发光聚合物的机遇与挑战：聚合物之美与聚集体之光相辉映［J］. 发光学报， 2020， 41（9）： 1082-1086. doi: 10.37188/fgxb20204109.1082http://dx.doi.org/10.37188/fgxb20204109.1082

QIN A J， HU R. Prospect and challenge of polymers featuring aggregation-induced emission characteristics ［J］. Chin. J. Lumin.， 2020， 41（9）： 1082-1086. （in Chinese）. doi: 10.37188/fgxb20204109.1082http://dx.doi.org/10.37188/fgxb20204109.1082

赵秋丽，卞洁鹏，杨庆浩，等. 聚集诱导发红光材料在生物成像领域的应用［J］. 材料导报， 2019， 33（3）： 522-535. doi: 10.11896/cldb.201903020http://dx.doi.org/10.11896/cldb.201903020

ZHAO Q L， BIAN J P， YANG Q H， et al. Application of aggregation-induced red emission materials in bioimaging ［J］. Mater. Rep.， 2019， 33（3）： 522-535. （in Chinese）. doi: 10.11896/cldb.201903020http://dx.doi.org/10.11896/cldb.201903020

LUO J D， XIE Z L， LAM J W Y， et al. Aggregation-induced emission of 1-methyl-1， 2， 3， 4， 5-pentaphenylsilole ［J］. Chem. Commun.， 2001，（18）： 1740-1741. doi: 10.1039/b105159hhttp://dx.doi.org/10.1039/b105159h

张双，秦安军，孙景志，等. 聚集诱导发光机理研究［J］. 化学进展， 2011， 23（4）： 623-636.

ZHANG S， QIN A J， SUN J Z， et al. Mechanism study of aggregation-induced emission ［J］. Prog. Chem.， 2011， 23（4）： 623-636. （in Chinese）

LI Q Q， LI Z. Molecular packing： another key point for the performance of organic and polymeric optoelectronic materials ［J］. Acc. Chem. Res.， 2020， 53（4）： 962-973. doi: 10.1021/acs.accounts.0c00060http://dx.doi.org/10.1021/acs.accounts.0c00060

刘瑞姣，曾竟，王慧. 基于四苯乙烯基的水杨醛缩芳胺希夫碱化合物的合成及性能研究［J］. 发光学报， 2017， 38（7）： 862-873. doi: 10.3788/fgxb20173807.0862http://dx.doi.org/10.3788/fgxb20173807.0862

LIU R J， ZENG J， WANG H. Synthesis and properties of salicyladehyde schiff-base derivatives based on tetraphenylethylene ［J］. Chin. J. Lumin.， 2017， 38（7）： 862-873. （in Chinese）. doi: 10.3788/fgxb20173807.0862http://dx.doi.org/10.3788/fgxb20173807.0862

赵秋丽，王金磊，杨庆浩，等. 烷基链长对四苯基乙烯衍生物聚集行为和光学性质的影响［J］. 材料导报， 2017， 31（8）： 6-10， 16. doi: 10.11896/j.issn.1005-023X.2017.08.002http://dx.doi.org/10.11896/j.issn.1005-023X.2017.08.002

ZHAO Q L， WANG J L， YANG Q H， et al. Effect of alkyl chain length on aggregation behaviors and optical properties of tetraphenylethene derivatives ［J］. Mater. Rep.， 2017， 31（8）： 6-10， 16. （in Chinese）. doi: 10.11896/j.issn.1005-023X.2017.08.002http://dx.doi.org/10.11896/j.issn.1005-023X.2017.08.002

CAI Z Y， WU X， LIU H， et al. Realizing record-high electroluminescence efficiency of 31.5% for red thermally activated delayed fluorescence molecules ［J］. Angew. Chem.， 2021， 133（44）： 23827-23832. doi: 10.1002/ange.202111172http://dx.doi.org/10.1002/ange.202111172

LIN G W， MANGHNANI P N， MAO D， et al. Robust red organic nanoparticles for in vivo fluorescence imaging of cancer cell progression in xenografted zebrafish ［J］. Adv. Funct. Mater.， 2017， 27（31）： 1701418-1-12. doi: 10.1002/adfm.201701418http://dx.doi.org/10.1002/adfm.201701418

CHANG Z F， JING L M， CHEN B， et al. Rational design of asymmetric red fluorescent probes for live cell imaging with high AIE effects and large two-photon absorption cross sections using tunable terminal groups ［J］. Chem. Sci.， 2016， 7（7）： 4527-4536. doi: 10.1039/c5sc04920bhttp://dx.doi.org/10.1039/c5sc04920b

CHEN J X， TAO W W， CHEN W C， et al. Red/near-infrared thermally activated delayed fluorescence OLEDs with near 100% internal quantum efficiency ［J］. Angew. Chem.， 2019， 131（41）： 14802-14807. doi: 10.1002/ange.201906575http://dx.doi.org/10.1002/ange.201906575

LIU Y， CHEN Y H， LI H， et al. High-performance solution-processed red thermally activated delayed fluorescence OLEDs employing aggregation-induced emission-active triazatruxene-based emitters ［J］. ACS Appl. Mater. Interfaces， 2020， 12（27）： 30652-30658. doi: 10.1021/acsami.0c07906http://dx.doi.org/10.1021/acsami.0c07906

Views

330

下载量

CSCD

Alert me when the article has been cited

提交

Tools

Publicity Resources

Conjugated Materials Containing Ethyl Benzoate Structure for Fluorescent Detection of Nitroaromatic Explosives

Application of NIR-Ⅱ Aggregation Induced Emission Materials in Surgical Navigation

Application of Tetraphenylene Aggregation-induced Emission Probes in Field of Biomolecular Detection

Research Progress of Stimuli-responsive AIE-active Hydrogels

Related Author

XING Yi-fan

SHI Ming-kai

LI Zhi-jun

DONG Lin-lin

ZHAO Shi-jie

XIE Tian-you

GUO Kun-peng

MIAO Yan-qin

Related Institution

School of Chemistry and Materials Science， Nanjing University of Information Science & Technology

School of Physics and Chemistry， Xihua University

College of Chemistry and Chemical Engineering， Northwest Normal University

School of Chemical Engineering， Lanzhou University of Arts and Science

Inner Mongolia Key Laboratory of Fine Organic Synthesis, College of Chemistry and Chemical Engineering, Inner Mongolia University

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