Abstract
This study examined the effect of chemical modifications on the spectral and lasing characteristics of truxene-cored starbursts as gain media for organic lasers. A series of conjugated starburst materials, consisting of a truxene core and oligofluorene bridges with and without diphenylamine (DPA), namely, TrXD and TrX, were assessed as model molecules to investigate the influence of DPA on the photophysical characteristics and organic lasing behaviors. TrXD with DPA could effectively restrain the aggregation and greatly suppress the aggregation-induced emission quenching, yielding high photoluminescence efficiency. A higher radiative decay rate kr was observed for TrXD than for TrX, suggesting that DPA is beneficial for enhancing the radiative decay process. TrXD showed low amplified spontaneous emission thresholds of 2.1–4.3 μJ cm−2 with high net gain coefficients of 80–101 cm−1, rather low loss coefficients of 2.6–4.4 cm−1, compared with TrX. The best performance with a lasing threshold of 0.31 kW cm−2 was obtained for Tr3D, which was superior to that of Tr3 (0.86 kW cm−2). The molecular systems with DPA have a large potential as attractive molecules for organic lasers because of the superior lasing properties induced by kr.
摘要
本文选取三并茚基多臂结构共轭大分子材料TrXD (二苯胺 (DPA)端基修饰)和TrX (DPA端基未修饰)为模型分子, 系统研究了 DPA修饰对三并茚基多臂结构共轭大分子激光增益材料光物理特性和 激光增益行为的影响. 在多臂结构分子中引入DPA基团可以有效抑制 聚集, 从而显著降低聚集诱导的发射猝灭, 进而提高发光效率. 同时, TrXD的辐射衰减速率kr高于TrX, 表明DPA修饰有利于增强辐射衰减 过程. 与TrX相比, TrXD具有较低的放大自发辐射阈值(2.1–4.3 μJ cm−2), 较高的净增益系数(80–101 cm−1), 较低的损耗系数 (2.6–4.4 cm−1). 其中, Tr3D具有优异的激光性能, 其激光阈值为 0.31 kW cm−2, 明显优于Tr3 (0.86 kW cm−2). 研究结果显示, DPA端基 修饰的多臂结构分子系统具有作为有机激光增益介质应用的更好潜 力, 这归因于其更高的辐射衰减速率kr, 从而表现出更优异的激光增益 特性.
Similar content being viewed by others
References
Song J, Lee H, Jeong EG, et al. Organic light-emitting diodes: Pushing toward the limits and beyond. Adv Mater, 2020, 32: 1907539
Liu CF, Liu X, Lai WY, et al. Organic light-emitting field-effect transistors: Device geometries and fabrication techniques. Adv Mater, 2018, 30: 1802466
Cheng P, Yang Y. Narrowing the band gap: The key to high-performance organic photovoltaics. Acc Chem Res, 2020, 53: 1218–1228
Jiang Y, Liu YY, Liu X, et al. Organic solid-state lasers: A materials view and future development. Chem Soc Rev, 2020, 49: 5885–5944
Jiang Y, Li KF, Gao K, et al. Frequency-upconverted stimulated emission by up to six-photon excitation from highly extended spiro-fused ladder-type oligo(p-phenylene)s. Angew Chem Int Ed, 2021, 60: 10007–10015
Samuel IDW, Turnbull GA. Organic semiconductor lasers. Chem Rev, 2007, 107: 1272–1295
Zhang W, Yao J, Zhao YS. Organic micro/nanoscale lasers. Acc Chem Res, 2016, 49: 1691–1700
Jiang Y, Lv P, Pan JQ, et al. Low-threshold organic semiconductor lasers with the aid of phosphorescent Ir(III) complexes as triplet sensitizers. Adv Funct Mater, 2019, 29: 1806719
Liu X, Sang M, Zhou J, et al. Pendant conjugated molecules based on a heterogeneous core structure with enhanced morphological and emissive properties for organic semiconductor lasing. Mater Chem Front, 2020, 4: 3660–3668
Liu CF, Lu T, Wang J, et al. Low threshold amplified spontaneous emission from efficient energy transfer in blends of conjugated polymers. J Phys Chem C, 2020, 124: 8576–8583
Xu FF, Li YJ, Lv Y, et al. Flat-panel laser displays based on liquid crystal microlaser arrays. CCS Chem, 2020, 2: 369–375
Qiao C, Zhang C, Zhou Z, et al. An optically reconfigurable Förster resonance energy transfer process for broadband switchable organic single-mode microlasers. CCS Chem, 2022, 4: 250–258
Dong H, Zhang C, Zhao YS. Controlling the output of organic micro/nanolasers. Adv Opt Mater, 2019, 7: 1900037
Qiao C, Zhang C, Zhou Z, et al. A photoisomerization-activated intramolecular charge-transfer process for broadband-tunable singlemode microlasers. Angew Chem, 2020, 132: 16126–16130
Wang K, Zhao YS. Pursuing electrically pumped lasing with organic semiconductors. Chem, 2021, 7: 3221–3231
Liang J, Chu M, Zhou Z, et al. Optically pumped lasing in microscale light-emitting electrochemical cell arrays for multicolor displays. Nano Lett, 2020, 20: 7116–7122
Ren JM, McKenzie TG, Fu Q, et al. Star polymers. Chem Rev, 2016, 116: 6743–6836
Liu CF, Liu X, Lai WY, et al. Design and synthesis of conjugated starburst molecules for optoelectronic applications. Chem Rec, 2019, 19: 1571–1595
Jarosz T, Lapkowski M, Ledwon P. Advances in star-shaped π-conjugated systems: Properties and applications. Macromol Rapid Commun, 2014, 35: 1006–1032
Detert H, Lehmann M, Meier H. Star-shaped conjugated systems. Materials, 2010, 3: 3218–3330
Xu W, Yi J, Lai WY, et al. Pyrene-capped conjugated amorphous starbursts: Synthesis, characterization, and stable lasing properties in ambient atmosphere. Adv Funct Mater, 2015, 25: 4617–4625
Jiu Y, Wang J, Yi J, et al. High-color-quality white electroluminescence and amplified spontaneous emission from a star-shaped single-polymer system with simultaneous three-color emission. Polym Chem, 2017, 8: 851–859
Li XC, Xue Y, Song W, et al. Highly regioselective direct C—H arylation: Facile construction of symmetrical dithienophthalimide-based π-conjugated molecules for optoelectronics. Research, 2020, 2020: 1–12
Kanibolotsky AL, Perepichka IF, Skabara PJ. Star-shaped π-conjugated oligomers and their applications in organic electronics and photonics. Chem Soc Rev, 2010, 39: 2695–2728
Lai WY, Xia R, He QY, et al. Enhanced solid-state luminescence and low-threshold lasing from starburst macromolecular materials. Adv Mater, 2009, 21: 355–360
Li XC, Wang CY, Lai WY, et al. Triazatruxene-based materials for organic electronics and optoelectronics. J Mater Chem C, 2016, 4: 10574–10587
Liu CF, Lu T, Lai WY, et al. Low-threshold non-doped deep blue lasing from monodisperse truxene-cored conjugated starbursts with high photostability. Chem Asian J, 2019, 14: 3442–3448
Huang H, Fu Q, Zhuang S, et al. Solution-processable 1,3,5-tri(9-anthracene)-benzene cored propeller-shaped materials with high Tg for blue organic light-emitting diodes. Org Electron, 2011, 12: 1716–1723
Liu CF, Sang M, Lai WY, et al. Design and synthesis of monodisperse macromolecular starbursts based on a triazine center with multi-branched oligofluorenes as efficient gain media for organic lasers. Macromolecules, 2018, 51: 1325–1335
Liu X, Sang M, Lin H, et al. Donor-acceptor type pendant conjugated molecules based on a triazine center with depressed intramolecular charge transfer characteristics as gain media for organic semiconductor lasers. Chem Eur J, 2020, 26: 3103–3112
Ren S, Zeng D, Zhong H, et al. Star-shaped donor-π-acceptor conjugated oligomers with 1,3,5-triazine cores: Convergent synthesis and multifunctional properties. J Phys Chem B, 2010, 114: 10374–10383
Zhang H, Lu TT, Lai WY, et al. Pyrene-cored starburst oligofluorenes with diphenylamine end-cappers: Design, synthesis, stabilized optical gain, and lasing properties. J Phys Chem C, 2017, 121: 27569–27579
Zhang H, Liu X, Lu TT, et al. Monodisperse six-armed starbursts based on truxene-cored multibranched oligofluorenes: Design, synthesis, and stabilized lasing characteristics. Chem Eur J, 2019, 25: 3909–3917
Gong Y, Zhan X, Li Q, et al. Progress of pyrene-based organic semiconductor in organic field effect transistors. Sci China Chem, 2016, 59: 1623–1631
Diab HM, Abdelmoniem AM, Shaaban MR, et al. An overview on synthetic strategies for the construction of star-shaped molecules. RSC Adv, 2019, 9: 16606–16682
Fang M, Huang J, Zhang Y, et al. Pyrene-centered cyanophenyl end-capped starbursts: Design, synthesis, stabilized blue electroluminescence and lasing properties. Mater Chem Front, 2017, 1: 668–676
Lai WY, He QY, Zhu R, et al. Kinked star-shaped fluorene/triazatruxene co-oligomer hybrids with enhanced functional properties for high-performance, solution-processed, blue organic light-emitting diodes. Adv Funct Mater, 2008, 18: 265–276
Nakanotani H, Furukawa T, Adachi C. Light amplification in an organic solid-state film with the aid of triplet-to-singlet upconversion. Adv Opt Mater, 2015, 3: 1381–1388
Liu QD, Lu J, Ding J, et al. Monodisperse starburst oligofluorenefunctionalized 4,4′,4″-tris(carbazol-9-yl)-triphenylamines: Their synthesis and deep-blue fluorescent properties for organic light-emitting diode applications. Adv Funct Mater, 2007, 17: 1028–1036
Iwan A, Sek D. Polymers with triphenylamine units: Photonic and electroactive materials. Prog Polym Sci, 2011, 36: 1277–1325
Liu C, Fu Q, Zou Y, et al. Low turn-on voltage, high-power-efficiency, solution-processed deep-blue organic light-emitting diodes based on starburst oligofluorenes with diphenylamine end-capper to enhance the HOMO level. Chem Mater, 2014, 26: 3074–3083
Guo L, Li KF, Zhang X, et al. Highly efficient multiphoton-pumped frequency-upconversion stimulated blue emission with ultralow threshold from highly extended ladder-type oligo(p-phenylene)s. Angew Chem Int Ed, 2016, 55: 10639–10644
Fang M, Huang J, Chang SJ, et al. Ladder-type oligo(p-phenylene)s with D-π-A architectures: Design, synthesis, optical gain properties, and stabilized amplified spontaneous emission. J Mater Chem C, 2017, 5: 5797–5809
Wu IY, Lin JT, Tao YT, et al. Diphenylthienylamine-based star-shaped molecules for electroluminescence applications. Chem Mater, 2001, 13: 2626–2631 Guo L, Li KF, et al. Exceptionally strong multiphoton-excited blue photoluminescence and lasing from ladder-type oligo(p-phenylene)s. J Am Chem Soc, 2012, 134: 7297–7300
Cekaviciute M, Simokaitiene J, Jankauskas V, et al. Structure-properties relationship of phenylethenyl-substituted triphenylamines. J Phys Chem C, 2013, 117: 7973–7980
Komori T, Nakanotani H, Yasuda T, et al. Light-emitting organic field-effect transistors based on highly luminescent single crystals of thiophene/phenylene co-oligomers. J Mater Chem C, 2014, 2: 4918–4921
Lu T, Chen F. Multiwfn: A multifunctional wavefunction analyzer. J Comput Chem, 2012, 33: 580–592
Jiang G, Li F, Kong X, et al. Suppression of aggregation caused quenching in U-shaped thermally activated delayed fluorescence molecules: Tert-butyl effect. J Lumin, 2020, 219: 116899
Cho YJ, Jeon SK, Lee SS, et al. Donor interlocked molecular design for fluorescence-like narrow emission in deep blue thermally activated delayed fluorescent emitters. Chem Mater, 2016, 28: 5400–5405
Aimono T, Kawamura Y, Goushi K, et al. 100% fluorescence efficiency of 4,4′-bis[(N-carbazole)styryl]biphenyl in a solid film and the very low amplified spontaneous emission threshold. Appl Phys Lett, 2005, 86: 071110
Gramlich M, Lampe C, Drewniok J, et al. How exciton-phonon coupling impacts photoluminescence in halide perovskite nanoplatelets. J Phys Chem Lett, 2021, 12: 11371–11377
Furukawa M, Mizuno K, Matsui A, et al. Time-resolved excitonic luminescence processes in poly(phenylenevinylene). J Phys Soc Jpn, 1989, 58: 2976–2987
Chen DY, Liu W, Zheng CJ, et al. Isomeric thermally activated delayed fluorescence emitters for color purity-improved emission in organic light-emitting devices. ACS Appl Mater Interfaces, 2016, 8: 16791–16798
Li W, Yao L, Liu H, et al. Highly efficient deep-blue OLED with an extraordinarily narrow FHWM of 35 nm and a y coordinate <0.05 based on a fully twisting donor-acceptor molecule. J Mater Chem C, 2014, 2: 4733–4736
Cerdán L. Variable stripe length method: Influence of stripe length choice on measured optical gain. Opt Lett, 2017, 42: 5258–5261
McGehee MD, Gupta R, Veenstra S, et al. Amplified spontaneous emission from photopumped films of a conjugated polymer. Phys Rev B, 1998, 58: 7035–7039
Peng F, Guo T, Ying L, et al. Improving electroluminescent performance of blue light-emitting poly(fluorene-co-dibenzothiophene-S,S-dioxide) by end-capping. Org Electron, 2017, 48: 118–126
Fell VHK, Findlay NJ, Breig B, et al. Effect of end group functionalisation of small molecules featuring the fluorine-thiophene-benzothiadiazole motif as emitters in solution-processed red and orange organic light-emitting diodes. J Mater Chem C, 2019, 7: 3934–3944
Silvast WT. Laser Fundamentals. Cambridge: Cambridge University Press, 2004
Acknowledgements
This work was supported by the National Natural Science Foundation of China (21835003, 91833304, 21422402, 21604043, 21674050, and 62004106), the National Key Basic Research Program of China (973 Program, 2014CB648300 and 2017YFB0404501), the Natural Science Foundation of Jiangsu Province (BK20160888 and BE2019120), the Program for Jiangsu Specially-Appointed Professor (RK030STP15001), the Six Talent Peaks Project of Jiangsu Province (TD-XCL-009), the 333 Project of Jiangsu Province (BRA2017402), the Natural Science Foundation of the Jiangsu Higher Education Institutions of China (20KJB140005), China Postdoctoral Science Foundation (2020M671553), the NUPT “1311 Project” and Scientific Foundation (NY217169, NY215062, NY215107, and NY217087), the Leading Talent of Technological Innovation of National Ten-Thousands Talents Program of China, the Excellent Scientific and Technological Innovative Teams of Jiangsu Higher Education Institutions (TJ217038), the Postgraduate Research & Practice Innovation Program of Jiangsu Province (SJCX21-0297), the Synergetic Innovation Center for Organic Electronics and Information Displays, and the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).
Author information
Authors and Affiliations
Contributions
Liu CF, Yu Q, Lu T, and Luo Q performed the experiments; Chen S, Guo Z, and Liu X participated in the discussions and data analysis. Liu CF wrote the draft, and Lai WY revised the manuscript. Lai WY contributed to the overall experimental design and supervised the project. All authors discussed the results and commented on the manuscript.
Corresponding author
Additional information
Conflict of interest
The authors declare that they have no conflict of interest.
Supplementary information
Supporting data are available in the online version of the paper.
Cheng-Fang Liu is an associate professor at Nanjing University of Posts and Telecommunications. She obtained her PhD degree from Changchun Institute of Applied Chemistry, Chinese Academy of Sciences in 2013. She then joined the Key Laboratory for Organic Electronics & Information Displays and Institute of Advanced Materials (IAM), Nanjing University of Posts & Telecommunications. Her current research interests are organic devices and thin-film growth.
Wen-Yong Lai is a full professor at Nanjing University of Posts and Telecommunications. He received his PhD degree from Fudan University in 2007. He then joined the State Key Laboratory of Organic Electronics & Information Displays and IAM, Nanjing University of Posts & Telecommunications. His research focuses on the design, synthesis, and application of organic and polymer optoelectronic materials for organic/plastic electronics, as well as the exploration of novel materials and processes for printed electronics and flexible electronics.
Supporting Information
40843_2022_2130_MOESM1_ESM.pdf
Effect of structural modifications on the spectral and lasing characteristics of truxene-cored starbursts with/without diphenylamine end-cappers
Rights and permissions
About this article
Cite this article
Liu, CF., Yu, Q., Lu, T. et al. Effect of structural modifications on the spectral and lasing characteristics of truxene-cored starbursts with/without diphenylamine end-cappers. Sci. China Mater. 66, 309–318 (2023). https://doi.org/10.1007/s40843-022-2130-2
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s40843-022-2130-2